chore(release): v0.11.3

refactor: simplify daily quota error messages
fix(core): ensure loop detection respects session disable flag (#12347 )
2026-08-02 13:11:03 -07:00 · 2025-10-31 20:24:24 +00:00 · 2025-10-31 11:11:19 -07:00 · 2025-10-31 10:31:04 -07:00 · 2025-10-31 10:31:03 -07:00 · 2025-10-31 10:31:02 -07:00
27 changed files with 816 additions and 836 deletions
@@ -473,21 +473,6 @@ a few things you can try in order of recommendation:
    "loadMemoryFromIncludeDirectories": true
    ```

- **`chatCompression`** (object):
-  - **Description:** Controls the settings for chat history compression, both
-    automatic and when manually invoked through the /compress command.
-  - **Properties:**
-    - **`contextPercentageThreshold`** (number): A value between 0 and 1 that
-      specifies the token threshold for compression as a percentage of the
-      model's total token limit. For example, a value of `0.6` will trigger
-      compression when the chat history exceeds 60% of the token limit.
-  - **Example:**
-    ```json
-    "chatCompression": {
-      "contextPercentageThreshold": 0.6
-    }
-    ```
-
 - **`showLineNumbers`** (boolean):
  - **Description:** Controls whether line numbers are displayed in code blocks
    in the CLI output.
@@ -244,13 +244,13 @@ their corresponding top-level category object in your `settings.json` file.
    example `{"run_shell_command": {"tokenBudget": 2000}}`
  - **Default:** `undefined`

- **`model.chatCompression.contextPercentageThreshold`** (number):
+- **`model.compressionThreshold`** (number):
  - **Description:** Sets the threshold for chat history compression as a
-    percentage of the model's total token limit. This is a value between 0 and 1
+    fraction of the model's total token limit. This is a value between 0 and 1
    that applies to both automatic compression and the manual `/compress`
    command. For example, a value of `0.6` will trigger compression when the
    chat history exceeds 60% of the token limit.
-  - **Default:** `0.7`
+  - **Default:** `0.2`

 - **`model.skipNextSpeakerCheck`** (boolean):
  - **Description:** Skip the next speaker check.
@@ -1,12 +1,12 @@
 {
  "name": "@google/gemini-cli",
-  "version": "0.11.1",
+  "version": "0.11.3",
  "lockfileVersion": 3,
  "requires": true,
  "packages": {
    "": {
      "name": "@google/gemini-cli",
-      "version": "0.11.1",
+      "version": "0.11.3",
      "workspaces": [
        "packages/*"
      ],
@@ -17669,7 +17669,7 @@
    },
    "packages/a2a-server": {
      "name": "@google/gemini-cli-a2a-server",
-      "version": "0.11.1",
+      "version": "0.11.3",
      "dependencies": {
        "@a2a-js/sdk": "^0.3.2",
        "@google-cloud/storage": "^7.16.0",
@@ -17943,7 +17943,7 @@
    },
    "packages/cli": {
      "name": "@google/gemini-cli",
-      "version": "0.11.1",
+      "version": "0.11.3",
      "dependencies": {
        "@google/gemini-cli-core": "file:../core",
        "@google/genai": "1.16.0",
@@ -18056,7 +18056,7 @@
    },
    "packages/core": {
      "name": "@google/gemini-cli-core",
-      "version": "0.11.1",
+      "version": "0.11.3",
      "dependencies": {
        "@google-cloud/logging": "^11.2.1",
        "@google-cloud/opentelemetry-cloud-monitoring-exporter": "^0.21.0",
@@ -18197,7 +18197,7 @@
    },
    "packages/test-utils": {
      "name": "@google/gemini-cli-test-utils",
-      "version": "0.11.1",
+      "version": "0.11.3",
      "license": "Apache-2.0",
      "devDependencies": {
        "typescript": "^5.3.3"
@@ -18208,7 +18208,7 @@
    },
    "packages/vscode-ide-companion": {
      "name": "gemini-cli-vscode-ide-companion",
-      "version": "0.11.1",
+      "version": "0.11.3",
      "license": "LICENSE",
      "dependencies": {
        "@modelcontextprotocol/sdk": "^1.15.1",
@@ -1,6 +1,6 @@
 {
  "name": "@google/gemini-cli",
-  "version": "0.11.1",
+  "version": "0.11.3",
  "engines": {
    "node": ">=20.0.0"
  },
@@ -14,7 +14,7 @@
    "url": "git+https://github.com/google-gemini/gemini-cli.git"
  },
  "config": {
-    "sandboxImageUri": "us-docker.pkg.dev/gemini-code-dev/gemini-cli/sandbox:0.11.1"
+    "sandboxImageUri": "us-docker.pkg.dev/gemini-code-dev/gemini-cli/sandbox:0.11.3"
  },
  "scripts": {
    "start": "cross-env NODE_ENV=development node scripts/start.js",
@@ -1,6 +1,6 @@
 {
  "name": "@google/gemini-cli-a2a-server",
-  "version": "0.11.1",
+  "version": "0.11.3",
  "description": "Gemini CLI A2A Server",
  "repository": {
    "type": "git",
@@ -1,6 +1,6 @@
 {
  "name": "@google/gemini-cli",
-  "version": "0.11.1",
+  "version": "0.11.3",
  "description": "Gemini CLI",
  "repository": {
    "type": "git",
@@ -25,7 +25,7 @@
    "dist"
  ],
  "config": {
-    "sandboxImageUri": "us-docker.pkg.dev/gemini-code-dev/gemini-cli/sandbox:0.11.1"
+    "sandboxImageUri": "us-docker.pkg.dev/gemini-code-dev/gemini-cli/sandbox:0.11.3"
  },
  "dependencies": {
    "@google/gemini-cli-core": "file:../core",
@@ -1572,7 +1572,7 @@ describe('loadCliConfig with includeDirectories', () => {
  });
 });

-describe('loadCliConfig chatCompression', () => {
+describe('loadCliConfig compressionThreshold', () => {
  const originalArgv = process.argv;

  beforeEach(() => {
@@ -1587,28 +1587,24 @@ describe('loadCliConfig chatCompression', () => {
    vi.restoreAllMocks();
  });

-  it('should pass chatCompression settings to the core config', async () => {
+  it('should pass settings to the core config', async () => {
    process.argv = ['node', 'script.js'];
    const argv = await parseArguments({} as Settings);
    const settings: Settings = {
      model: {
-        chatCompression: {
-          contextPercentageThreshold: 0.5,
-        },
+        compressionThreshold: 0.5,
      },
    };
    const config = await loadCliConfig(settings, [], 'test-session', argv);
-    expect(config.getChatCompression()).toEqual({
-      contextPercentageThreshold: 0.5,
-    });
+    expect(config.getCompressionThreshold()).toEqual(0.5);
  });

-  it('should have undefined chatCompression if not in settings', async () => {
+  it('should have undefined compressionThreshold if not in settings', async () => {
    process.argv = ['node', 'script.js'];
    const argv = await parseArguments({} as Settings);
    const settings: Settings = {};
    const config = await loadCliConfig(settings, [], 'test-session', argv);
-    expect(config.getChatCompression()).toBeUndefined();
+    expect(config.getCompressionThreshold()).toBeUndefined();
  });
 });

@@ -610,7 +610,7 @@ export async function loadCliConfig(
    noBrowser: !!process.env['NO_BROWSER'],
    summarizeToolOutput: settings.model?.summarizeToolOutput,
    ideMode,
-    chatCompression: settings.model?.chatCompression,
+    compressionThreshold: settings.model?.compressionThreshold,
    folderTrust,
    interactive,
    trustedFolder,
@@ -1051,15 +1051,15 @@ describe('Settings Loading and Merging', () => {
      });
    });

-    it('should merge chatCompression settings, with workspace taking precedence', () => {
+    it('should merge compressionThreshold settings, with workspace taking precedence', () => {
      (mockFsExistsSync as Mock).mockReturnValue(true);
      const userSettingsContent = {
        general: {},
-        model: { chatCompression: { contextPercentageThreshold: 0.5 } },
+        model: { compressionThreshold: 0.5 },
      };
      const workspaceSettingsContent = {
        general: {},
-        model: { chatCompression: { contextPercentageThreshold: 0.8 } },
+        model: { compressionThreshold: 0.8 },
      };

      (fs.readFileSync as Mock).mockImplementation(
@@ -1074,15 +1074,11 @@ describe('Settings Loading and Merging', () => {

      const settings = loadSettings(MOCK_WORKSPACE_DIR);

-      expect(settings.user.settings.model?.chatCompression).toEqual({
-        contextPercentageThreshold: 0.5,
-      });
-      expect(settings.workspace.settings.model?.chatCompression).toEqual({
-        contextPercentageThreshold: 0.8,
-      });
-      expect(settings.merged.model?.chatCompression).toEqual({
-        contextPercentageThreshold: 0.8,
-      });
+      expect(settings.user.settings.model?.compressionThreshold).toEqual(0.5);
+      expect(settings.workspace.settings.model?.compressionThreshold).toEqual(
+        0.8,
+      );
+      expect(settings.merged.model?.compressionThreshold).toEqual(0.8);
    });

    it('should merge output format settings, with workspace taking precedence', () => {
@@ -1109,13 +1105,13 @@ describe('Settings Loading and Merging', () => {
      expect(settings.merged.output?.format).toBe('json');
    });

-    it('should handle chatCompression when only in user settings', () => {
+    it('should handle compressionThreshold when only in user settings', () => {
      (mockFsExistsSync as Mock).mockImplementation(
        (p: fs.PathLike) => p === USER_SETTINGS_PATH,
      );
      const userSettingsContent = {
        general: {},
-        model: { chatCompression: { contextPercentageThreshold: 0.5 } },
+        model: { compressionThreshold: 0.5 },
      };
      (fs.readFileSync as Mock).mockImplementation(
        (p: fs.PathOrFileDescriptor) => {
@@ -1126,9 +1122,7 @@ describe('Settings Loading and Merging', () => {
      );

      const settings = loadSettings(MOCK_WORKSPACE_DIR);
-      expect(settings.merged.model?.chatCompression).toEqual({
-        contextPercentageThreshold: 0.5,
-      });
+      expect(settings.merged.model?.compressionThreshold).toEqual(0.5);
    });

    it('should have model as undefined if not in any settings file', () => {
@@ -1138,39 +1132,15 @@ describe('Settings Loading and Merging', () => {
      expect(settings.merged.model).toBeUndefined();
    });

-    it('should ignore chatCompression if contextPercentageThreshold is invalid', () => {
-      const warnSpy = vi.spyOn(console, 'warn').mockImplementation(() => {});
-      (mockFsExistsSync as Mock).mockImplementation(
-        (p: fs.PathLike) => p === USER_SETTINGS_PATH,
-      );
-      const userSettingsContent = {
-        general: {},
-        model: { chatCompression: { contextPercentageThreshold: 1.5 } },
-      };
-      (fs.readFileSync as Mock).mockImplementation(
-        (p: fs.PathOrFileDescriptor) => {
-          if (p === USER_SETTINGS_PATH)
-            return JSON.stringify(userSettingsContent);
-          return '{}';
-        },
-      );
-
-      const settings = loadSettings(MOCK_WORKSPACE_DIR);
-      expect(settings.merged.model?.chatCompression).toEqual({
-        contextPercentageThreshold: 1.5,
-      });
-      warnSpy.mockRestore();
-    });
-
-    it('should deep merge chatCompression settings', () => {
+    it('should use user compressionThreshold if workspace does not define it', () => {
      (mockFsExistsSync as Mock).mockReturnValue(true);
      const userSettingsContent = {
        general: {},
-        model: { chatCompression: { contextPercentageThreshold: 0.5 } },
+        model: { compressionThreshold: 0.5 },
      };
      const workspaceSettingsContent = {
        general: {},
-        model: { chatCompression: {} },
+        model: {},
      };

      (fs.readFileSync as Mock).mockImplementation(
@@ -1185,9 +1155,7 @@ describe('Settings Loading and Merging', () => {

      const settings = loadSettings(MOCK_WORKSPACE_DIR);

-      expect(settings.merged.model?.chatCompression).toEqual({
-        contextPercentageThreshold: 0.5,
-      });
+      expect(settings.merged.model?.compressionThreshold).toEqual(0.5);
    });

    it('should merge includeDirectories from all scopes', () => {
@@ -1972,9 +1940,6 @@ describe('Settings Loading and Merging', () => {
        },
        model: {
          name: 'gemini-pro',
-          chatCompression: {
-            contextPercentageThreshold: 0.5,
-          },
        },
        mcpServers: {
          'server-1': {
@@ -1993,9 +1958,6 @@ describe('Settings Loading and Merging', () => {
          myTheme: {},
        },
        model: 'gemini-pro',
-        chatCompression: {
-          contextPercentageThreshold: 0.5,
-        },
        mcpServers: {
          'server-1': {
            command: 'node server.js',
@@ -2035,9 +1997,6 @@ describe('Settings Loading and Merging', () => {
        },
        model: {
          name: 'gemini-pro',
-          chatCompression: {
-            contextPercentageThreshold: 0.8,
-          },
        },
        context: {
          fileName: 'CONTEXT.md',
@@ -2077,9 +2036,6 @@ describe('Settings Loading and Merging', () => {
        theme: 'dark',
        usageStatisticsEnabled: false,
        model: 'gemini-pro',
-        chatCompression: {
-          contextPercentageThreshold: 0.8,
-        },
        contextFileName: 'CONTEXT.md',
        includeDirectories: ['/src'],
        sandbox: true,
@@ -64,7 +64,7 @@ const MIGRATION_MAP: Record<string, string> = {
  autoAccept: 'tools.autoAccept',
  autoConfigureMaxOldSpaceSize: 'advanced.autoConfigureMemory',
  bugCommand: 'advanced.bugCommand',
-  chatCompression: 'model.chatCompression',
+  chatCompression: 'model.compressionThreshold',
  checkpointing: 'general.checkpointing',
  coreTools: 'tools.core',
  contextFileName: 'context.fileName',
@@ -159,6 +159,10 @@ describe('SettingsSchema', () => {
      expect(
        getSettingsSchema().ui.properties.showMemoryUsage.showInDialog,
      ).toBe(true);
+      expect(
+        getSettingsSchema().ui.properties.footer.properties
+          .hideContextPercentage.showInDialog,
+      ).toBe(true);
      expect(getSettingsSchema().general.properties.vimMode.showInDialog).toBe(
        true,
      );
@@ -14,7 +14,6 @@ import type {
  BugCommandSettings,
  TelemetrySettings,
  AuthType,
-  ChatCompressionSettings,
 } from '@google/gemini-cli-core';
 import {
  DEFAULT_TRUNCATE_TOOL_OUTPUT_LINES,
@@ -389,6 +388,15 @@ const SETTINGS_SCHEMA = {
            description: 'Hide the model name and context usage in the footer.',
            showInDialog: true,
          },
+          hideContextPercentage: {
+            type: 'boolean',
+            label: 'Hide Context Window Percentage',
+            category: 'UI',
+            requiresRestart: false,
+            default: true,
+            description: 'Hides the context window remaining percentage.',
+            showInDialog: true,
+          },
        },
      },
      hideFooter: {
@@ -578,14 +586,15 @@ const SETTINGS_SCHEMA = {
        description: 'Settings for summarizing tool output.',
        showInDialog: false,
      },
-      chatCompression: {
-        type: 'object',
-        label: 'Chat Compression',
+      compressionThreshold: {
+        type: 'number',
+        label: 'Compression Threshold',
        category: 'Model',
-        requiresRestart: false,
-        default: undefined as ChatCompressionSettings | undefined,
-        description: 'Chat compression settings.',
-        showInDialog: false,
+        requiresRestart: true,
+        default: 0.2 as number,
+        description:
+          'The fraction of context usage at which to trigger context compression (e.g. 0.2, 0.3).',
+        showInDialog: true,
      },
      skipNextSpeakerCheck: {
        type: 'boolean',
@@ -4,6 +4,7 @@
 * SPDX-License-Identifier: Apache-2.0
 */

+import { describe, it, expect, vi } from 'vitest';
 import {
  renderWithProviders,
  createMockSettings,
@@ -120,6 +121,13 @@ describe('<Footer />', () => {
    const { lastFrame } = renderWithProviders(<Footer />, {
      width: 120,
      uiState: { sessionStats: mockSessionStats },
+      settings: createMockSettings({
+        ui: {
+          footer: {
+            hideContextPercentage: false,
+          },
+        },
+      }),
    });
    expect(lastFrame()).toContain(defaultProps.model);
    expect(lastFrame()).toMatch(/\(\d+% context left\)/);
@@ -129,6 +137,13 @@ describe('<Footer />', () => {
    const { lastFrame } = renderWithProviders(<Footer />, {
      width: 99,
      uiState: { sessionStats: mockSessionStats },
+      settings: createMockSettings({
+        ui: {
+          footer: {
+            hideContextPercentage: false,
+          },
+        },
+      }),
    });
    expect(lastFrame()).toContain(defaultProps.model);
    expect(lastFrame()).toMatch(/\(\d+%\)/);
@@ -192,6 +207,13 @@ describe('<Footer />', () => {
      const { lastFrame } = renderWithProviders(<Footer />, {
        width: 120,
        uiState: { sessionStats: mockSessionStats },
+        settings: createMockSettings({
+          ui: {
+            footer: {
+              hideContextPercentage: false,
+            },
+          },
+        }),
      });
      expect(lastFrame()).toMatchSnapshot('complete-footer-wide');
    });
@@ -247,10 +269,49 @@ describe('<Footer />', () => {
      expect(lastFrame()).toMatchSnapshot('footer-only-sandbox');
    });

+    it('hides the context percentage when hideContextPercentage is true', () => {
+      const { lastFrame } = renderWithProviders(<Footer />, {
+        width: 120,
+        uiState: { sessionStats: mockSessionStats },
+        settings: createMockSettings({
+          ui: {
+            footer: {
+              hideContextPercentage: true,
+            },
+          },
+        }),
+      });
+      expect(lastFrame()).toContain(defaultProps.model);
+      expect(lastFrame()).not.toMatch(/\(\d+% context left\)/);
+    });
+
+    it('shows the context percentage when hideContextPercentage is false', () => {
+      const { lastFrame } = renderWithProviders(<Footer />, {
+        width: 120,
+        uiState: { sessionStats: mockSessionStats },
+        settings: createMockSettings({
+          ui: {
+            footer: {
+              hideContextPercentage: false,
+            },
+          },
+        }),
+      });
+      expect(lastFrame()).toContain(defaultProps.model);
+      expect(lastFrame()).toMatch(/\(\d+% context left\)/);
+    });
+
    it('renders complete footer in narrow terminal (baseline narrow)', () => {
      const { lastFrame } = renderWithProviders(<Footer />, {
        width: 79,
        uiState: { sessionStats: mockSessionStats },
+        settings: createMockSettings({
+          ui: {
+            footer: {
+              hideContextPercentage: false,
+            },
+          },
+        }),
      });
      expect(lastFrame()).toMatchSnapshot('complete-footer-narrow');
    });
@@ -61,6 +61,8 @@ export const Footer: React.FC = () => {
  const hideSandboxStatus =
    settings.merged.ui?.footer?.hideSandboxStatus || false;
  const hideModelInfo = settings.merged.ui?.footer?.hideModelInfo || false;
+  const hideContextPercentage =
+    settings.merged.ui?.footer?.hideContextPercentage ?? true;

  const pathLength = Math.max(20, Math.floor(mainAreaWidth * 0.25));
  const displayPath = shortenPath(tildeifyPath(targetDir), pathLength);
@@ -146,12 +148,17 @@ export const Footer: React.FC = () => {
        <Box alignItems="center" justifyContent="flex-end">
          <Box alignItems="center">
            <Text color={theme.text.accent}>
-              {model}{' '}
-              <ContextUsageDisplay
-                promptTokenCount={promptTokenCount}
-                model={model}
-                terminalWidth={mainAreaWidth}
-              />
+              {model}
+              {!hideContextPercentage && (
+                <>
+                  {' '}
+                  <ContextUsageDisplay
+                    promptTokenCount={promptTokenCount}
+                    model={model}
+                    terminalWidth={mainAreaWidth}
+                  />
+                </>
+              )}
            </Text>
            {showMemoryUsage && <MemoryUsageDisplay />}
          </Box>
@@ -1,6 +1,6 @@
 {
  "name": "@google/gemini-cli-core",
-  "version": "0.11.1",
+  "version": "0.11.3",
  "description": "Gemini CLI Core",
  "repository": {
    "type": "git",
@@ -581,7 +581,7 @@ describe('Server Config (config.ts)', () => {
        useModelRouter: true,
      });
      await config.refreshAuth(AuthType.LOGIN_WITH_GOOGLE);
-      expect(config.getUseModelRouter()).toBe(false);
+      expect(config.getUseModelRouter()).toBe(true);
    });

    it('should enable model router by default for other auth types', async () => {
@@ -96,10 +96,6 @@ export interface BugCommandSettings {
  urlTemplate: string;
 }

-export interface ChatCompressionSettings {
-  contextPercentageThreshold?: number;
-}
-
 export interface SummarizeToolOutputSettings {
  tokenBudget?: number;
 }
@@ -261,7 +257,7 @@ export interface ConfigParameters {
  folderTrust?: boolean;
  ideMode?: boolean;
  loadMemoryFromIncludeDirectories?: boolean;
-  chatCompression?: ChatCompressionSettings;
+  compressionThreshold?: number;
  interactive?: boolean;
  trustedFolder?: boolean;
  useRipgrep?: boolean;
@@ -354,7 +350,7 @@ export class Config {
    | undefined;
  private readonly experimentalZedIntegration: boolean = false;
  private readonly loadMemoryFromIncludeDirectories: boolean = false;
-  private readonly chatCompression: ChatCompressionSettings | undefined;
+  private readonly compressionThreshold: number | undefined;
  private readonly interactive: boolean;
  private readonly ptyInfo: string;
  private readonly trustedFolder: boolean | undefined;
@@ -453,7 +449,7 @@ export class Config {
    this.ideMode = params.ideMode ?? false;
    this.loadMemoryFromIncludeDirectories =
      params.loadMemoryFromIncludeDirectories ?? false;
-    this.chatCompression = params.chatCompression;
+    this.compressionThreshold = params.compressionThreshold;
    this.interactive = params.interactive ?? false;
    this.ptyInfo = params.ptyInfo ?? 'child_process';
    this.trustedFolder = params.trustedFolder;
@@ -476,9 +472,7 @@ export class Config {
    this.useWriteTodos = params.useWriteTodos ?? false;
    this.initialUseModelRouter = params.useModelRouter ?? false;
    this.useModelRouter = this.initialUseModelRouter;
-    this.disableModelRouterForAuth = params.disableModelRouterForAuth ?? [
-      AuthType.LOGIN_WITH_GOOGLE,
-    ];
+    this.disableModelRouterForAuth = params.disableModelRouterForAuth ?? [];
    this.enableMessageBusIntegration =
      params.enableMessageBusIntegration ?? false;
    this.codebaseInvestigatorSettings = {
@@ -979,8 +973,8 @@ export class Config {
    this.fileSystemService = fileSystemService;
  }

-  getChatCompression(): ChatCompressionSettings | undefined {
-    return this.chatCompression;
+  getCompressionThreshold(): number | undefined {
+    return this.compressionThreshold;
  }

  isInteractiveShellEnabled(): boolean {
@@ -16,7 +16,6 @@ import {

 import type { Content, GenerateContentResponse, Part } from '@google/genai';
 import {
-  findCompressSplitPoint,
  isThinkingDefault,
  isThinkingSupported,
  GeminiClient,
@@ -40,9 +39,11 @@ import { FileDiscoveryService } from '../services/fileDiscoveryService.js';
 import { setSimulate429 } from '../utils/testUtils.js';
 import { tokenLimit } from './tokenLimits.js';
 import { ideContextStore } from '../ide/ideContext.js';
-import { ClearcutLogger } from '../telemetry/clearcut-logger/clearcut-logger.js';
 import type { ModelRouterService } from '../routing/modelRouterService.js';
 import { uiTelemetryService } from '../telemetry/uiTelemetry.js';
+import { ChatCompressionService } from '../services/chatCompressionService.js';
+
+vi.mock('../services/chatCompressionService.js');

 // Mock fs module to prevent actual file system operations during tests
 const mockFileSystem = new Map<string, string>();
@@ -132,83 +133,6 @@ async function fromAsync<T>(promise: AsyncGenerator<T>): Promise<readonly T[]> {
  return results;
 }

-describe('findCompressSplitPoint', () => {
-  it('should throw an error for non-positive numbers', () => {
-    expect(() => findCompressSplitPoint([], 0)).toThrow(
-      'Fraction must be between 0 and 1',
-    );
-  });
-
-  it('should throw an error for a fraction greater than or equal to 1', () => {
-    expect(() => findCompressSplitPoint([], 1)).toThrow(
-      'Fraction must be between 0 and 1',
-    );
-  });
-
-  it('should handle an empty history', () => {
-    expect(findCompressSplitPoint([], 0.5)).toBe(0);
-  });
-
-  it('should handle a fraction in the middle', () => {
-    const history: Content[] = [
-      { role: 'user', parts: [{ text: 'This is the first message.' }] }, // JSON length: 66 (19%)
-      { role: 'model', parts: [{ text: 'This is the second message.' }] }, // JSON length: 68 (40%)
-      { role: 'user', parts: [{ text: 'This is the third message.' }] }, // JSON length: 66 (60%)
-      { role: 'model', parts: [{ text: 'This is the fourth message.' }] }, // JSON length: 68 (80%)
-      { role: 'user', parts: [{ text: 'This is the fifth message.' }] }, // JSON length: 65 (100%)
-    ];
-    expect(findCompressSplitPoint(history, 0.5)).toBe(4);
-  });
-
-  it('should handle a fraction of last index', () => {
-    const history: Content[] = [
-      { role: 'user', parts: [{ text: 'This is the first message.' }] }, // JSON length: 66 (19%)
-      { role: 'model', parts: [{ text: 'This is the second message.' }] }, // JSON length: 68 (40%)
-      { role: 'user', parts: [{ text: 'This is the third message.' }] }, // JSON length: 66 (60%)
-      { role: 'model', parts: [{ text: 'This is the fourth message.' }] }, // JSON length: 68 (80%)
-      { role: 'user', parts: [{ text: 'This is the fifth message.' }] }, // JSON length: 65 (100%)
-    ];
-    expect(findCompressSplitPoint(history, 0.9)).toBe(4);
-  });
-
-  it('should handle a fraction of after last index', () => {
-    const history: Content[] = [
-      { role: 'user', parts: [{ text: 'This is the first message.' }] }, // JSON length: 66 (24%%)
-      { role: 'model', parts: [{ text: 'This is the second message.' }] }, // JSON length: 68 (50%)
-      { role: 'user', parts: [{ text: 'This is the third message.' }] }, // JSON length: 66 (74%)
-      { role: 'model', parts: [{ text: 'This is the fourth message.' }] }, // JSON length: 68 (100%)
-    ];
-    expect(findCompressSplitPoint(history, 0.8)).toBe(4);
-  });
-
-  it('should return earlier splitpoint if no valid ones are after threshhold', () => {
-    const history: Content[] = [
-      { role: 'user', parts: [{ text: 'This is the first message.' }] },
-      { role: 'model', parts: [{ text: 'This is the second message.' }] },
-      { role: 'user', parts: [{ text: 'This is the third message.' }] },
-      { role: 'model', parts: [{ functionCall: {} }] },
-    ];
-    // Can't return 4 because the previous item has a function call.
-    expect(findCompressSplitPoint(history, 0.99)).toBe(2);
-  });
-
-  it('should handle a history with only one item', () => {
-    const historyWithEmptyParts: Content[] = [
-      { role: 'user', parts: [{ text: 'Message 1' }] },
-    ];
-    expect(findCompressSplitPoint(historyWithEmptyParts, 0.5)).toBe(0);
-  });
-
-  it('should handle history with weird parts', () => {
-    const historyWithEmptyParts: Content[] = [
-      { role: 'user', parts: [{ text: 'Message 1' }] },
-      { role: 'model', parts: [{ fileData: { fileUri: 'derp' } }] },
-      { role: 'user', parts: [{ text: 'Message 2' }] },
-    ];
-    expect(findCompressSplitPoint(historyWithEmptyParts, 0.5)).toBe(2);
-  });
-});
-
 describe('isThinkingSupported', () => {
  it('should return true for gemini-2.5', () => {
    expect(isThinkingSupported('gemini-2.5')).toBe(true);
@@ -252,6 +176,15 @@ describe('Gemini Client (client.ts)', () => {
    vi.resetAllMocks();
    vi.mocked(uiTelemetryService.setLastPromptTokenCount).mockClear();

+    vi.mocked(ChatCompressionService.prototype.compress).mockResolvedValue({
+      newHistory: null,
+      info: {
+        originalTokenCount: 0,
+        newTokenCount: 0,
+        compressionStatus: CompressionStatus.NOOP,
+      },
+    });
+
    mockGenerateContentFn = vi.fn().mockResolvedValue({
      candidates: [{ content: { parts: [{ text: '{"key": "value"}' }] } }],
    });
@@ -404,7 +337,8 @@ describe('Gemini Client (client.ts)', () => {
        { role: 'model', parts: [{ text: 'Long response' }] },
      ] as Content[],
      originalTokenCount = 1000,
-      summaryText = 'This is a summary.',
+      newTokenCount = 500,
+      compressionStatus = CompressionStatus.COMPRESSED,
    } = {}) {
      const mockOriginalChat: Partial<GeminiChat> = {
        getHistory: vi.fn((_curated?: boolean) => chatHistory),
@@ -416,47 +350,25 @@ describe('Gemini Client (client.ts)', () => {
        originalTokenCount,
      );

-      mockGenerateContentFn.mockResolvedValue({
-        candidates: [
-          {
-            content: {
-              role: 'model',
-              parts: [{ text: summaryText }],
-            },
-          },
-        ],
-      } as unknown as GenerateContentResponse);
-
-      // Calculate what the new history will be
-      const splitPoint = findCompressSplitPoint(chatHistory, 0.7); // 1 - 0.3
-      const historyToKeep = chatHistory.slice(splitPoint);
-
-      // This is the history that the new chat will have.
-      // It includes the default startChat history + the extra history from tryCompressChat
-      const newCompressedHistory: Content[] = [
-        // Mocked envParts + canned response from startChat
-        {
-          role: 'user',
-          parts: [{ text: 'Mocked env context' }],
-        },
-        {
-          role: 'model',
-          parts: [{ text: 'Got it. Thanks for the context!' }],
-        },
-        // extraHistory from tryCompressChat
-        {
-          role: 'user',
-          parts: [{ text: summaryText }],
-        },
-        {
-          role: 'model',
-          parts: [{ text: 'Got it. Thanks for the additional context!' }],
-        },
-        ...historyToKeep,
+      const newHistory: Content[] = [
+        { role: 'user', parts: [{ text: 'Summary' }] },
+        { role: 'model', parts: [{ text: 'Got it' }] },
      ];

+      vi.mocked(ChatCompressionService.prototype.compress).mockResolvedValue({
+        newHistory:
+          compressionStatus === CompressionStatus.COMPRESSED
+            ? newHistory
+            : null,
+        info: {
+          originalTokenCount,
+          newTokenCount,
+          compressionStatus,
+        },
+      });
+
      const mockNewChat: Partial<GeminiChat> = {
-        getHistory: vi.fn().mockReturnValue(newCompressedHistory),
+        getHistory: vi.fn().mockReturnValue(newHistory),
        setHistory: vi.fn(),
      };

@@ -464,39 +376,32 @@ describe('Gemini Client (client.ts)', () => {
        .fn()
        .mockResolvedValue(mockNewChat as GeminiChat);

-      const totalChars = newCompressedHistory.reduce(
-        (total, content) => total + JSON.stringify(content).length,
-        0,
-      );
-      const estimatedNewTokenCount = Math.floor(totalChars / 4);
-
      return {
        client,
        mockOriginalChat,
        mockNewChat,
-        estimatedNewTokenCount,
+        estimatedNewTokenCount: newTokenCount,
      };
    }

    describe('when compression inflates the token count', () => {
      it('allows compression to be forced/manual after a failure', async () => {
-        // Call 1 (Fails): Setup with a long summary to inflate tokens
-        const longSummary = 'long summary '.repeat(100);
-        const { client, estimatedNewTokenCount: inflatedTokenCount } = setup({
+        // Call 1 (Fails): Setup with inflated tokens
+        setup({
          originalTokenCount: 100,
-          summaryText: longSummary,
+          newTokenCount: 200,
+          compressionStatus:
+            CompressionStatus.COMPRESSION_FAILED_INFLATED_TOKEN_COUNT,
        });
-        expect(inflatedTokenCount).toBeGreaterThan(100); // Ensure setup is correct

        await client.tryCompressChat('prompt-id-4', false); // Fails

-        // Call 2 (Forced): Re-setup with a short summary
-        const shortSummary = 'short';
+        // Call 2 (Forced): Re-setup with compressed tokens
        const { estimatedNewTokenCount: compressedTokenCount } = setup({
          originalTokenCount: 100,
-          summaryText: shortSummary,
+          newTokenCount: 50,
+          compressionStatus: CompressionStatus.COMPRESSED,
        });
-        expect(compressedTokenCount).toBeLessThanOrEqual(100); // Ensure setup is correct

        const result = await client.tryCompressChat('prompt-id-4', true); // Forced

@@ -508,12 +413,12 @@ describe('Gemini Client (client.ts)', () => {
      });

      it('yields the result even if the compression inflated the tokens', async () => {
-        const longSummary = 'long summary '.repeat(100);
        const { client, estimatedNewTokenCount } = setup({
          originalTokenCount: 100,
-          summaryText: longSummary,
+          newTokenCount: 200,
+          compressionStatus:
+            CompressionStatus.COMPRESSION_FAILED_INFLATED_TOKEN_COUNT,
        });
-        expect(estimatedNewTokenCount).toBeGreaterThan(100); // Ensure setup is correct

        const result = await client.tryCompressChat('prompt-id-4', false);

@@ -530,12 +435,12 @@ describe('Gemini Client (client.ts)', () => {
      });

      it('does not manipulate the source chat', async () => {
-        const longSummary = 'long summary '.repeat(100);
-        const { client, mockOriginalChat, estimatedNewTokenCount } = setup({
+        const { client, mockOriginalChat } = setup({
          originalTokenCount: 100,
-          summaryText: longSummary,
+          newTokenCount: 200,
+          compressionStatus:
+            CompressionStatus.COMPRESSION_FAILED_INFLATED_TOKEN_COUNT,
        });
-        expect(estimatedNewTokenCount).toBeGreaterThan(100); // Ensure setup is correct

        await client.tryCompressChat('prompt-id-4', false);

@@ -543,45 +448,65 @@ describe('Gemini Client (client.ts)', () => {
        expect(client['chat']).toBe(mockOriginalChat);
      });

-      it('will not attempt to compress context after a failure', async () => {
-        const longSummary = 'long summary '.repeat(100);
-        const { client, estimatedNewTokenCount } = setup({
+      it.skip('will not attempt to compress context after a failure', async () => {
+        const { client } = setup({
          originalTokenCount: 100,
-          summaryText: longSummary,
+          newTokenCount: 200,
+          compressionStatus:
+            CompressionStatus.COMPRESSION_FAILED_INFLATED_TOKEN_COUNT,
        });
-        expect(estimatedNewTokenCount).toBeGreaterThan(100); // Ensure setup is correct

        await client.tryCompressChat('prompt-id-4', false); // This fails and sets hasFailedCompressionAttempt = true

+        // Mock the next call to return NOOP
+        vi.mocked(
+          ChatCompressionService.prototype.compress,
+        ).mockResolvedValueOnce({
+          newHistory: null,
+          info: {
+            originalTokenCount: 0,
+            newTokenCount: 0,
+            compressionStatus: CompressionStatus.NOOP,
+          },
+        });
+
        // This call should now be a NOOP
        const result = await client.tryCompressChat('prompt-id-5', false);

-        // generateContent (for summary) should only have been called once
-        expect(mockGenerateContentFn).toHaveBeenCalledTimes(1);
-        expect(result).toEqual({
-          compressionStatus: CompressionStatus.NOOP,
-          newTokenCount: 0,
-          originalTokenCount: 0,
-        });
+        expect(result.compressionStatus).toBe(CompressionStatus.NOOP);
+        expect(ChatCompressionService.prototype.compress).toHaveBeenCalledTimes(
+          2,
+        );
+        expect(
+          ChatCompressionService.prototype.compress,
+        ).toHaveBeenLastCalledWith(
+          expect.anything(),
+          'prompt-id-5',
+          false,
+          expect.anything(),
+          expect.anything(),
+          true, // hasFailedCompressionAttempt
+        );
      });
    });

    it('should not trigger summarization if token count is below threshold', async () => {
      const MOCKED_TOKEN_LIMIT = 1000;
-      vi.mocked(tokenLimit).mockReturnValue(MOCKED_TOKEN_LIMIT);
-      mockGetHistory.mockReturnValue([
-        { role: 'user', parts: [{ text: '...history...' }] },
-      ]);
      const originalTokenCount = MOCKED_TOKEN_LIMIT * 0.699;
-      vi.mocked(uiTelemetryService.getLastPromptTokenCount).mockReturnValue(
-        originalTokenCount,
-      );
+
+      vi.mocked(ChatCompressionService.prototype.compress).mockResolvedValue({
+        newHistory: null,
+        info: {
+          originalTokenCount,
+          newTokenCount: originalTokenCount,
+          compressionStatus: CompressionStatus.NOOP,
+        },
+      });

      const initialChat = client.getChat();
      const result = await client.tryCompressChat('prompt-id-2', false);
      const newChat = client.getChat();

-      expect(tokenLimit).toHaveBeenCalled();
      expect(result).toEqual({
        compressionStatus: CompressionStatus.NOOP,
        newTokenCount: originalTokenCount,
@@ -594,6 +519,8 @@ describe('Gemini Client (client.ts)', () => {
      const { client } = setup({
        chatHistory: [{ role: 'user', parts: [{ text: 'hi' }] }],
        originalTokenCount: 50,
+        newTokenCount: 50,
+        compressionStatus: CompressionStatus.NOOP,
      });

      const result = await client.tryCompressChat('prompt-id-noop', false);
@@ -603,337 +530,6 @@ describe('Gemini Client (client.ts)', () => {
        originalTokenCount: 50,
        newTokenCount: 50,
      });
-      expect(mockGenerateContentFn).not.toHaveBeenCalled();
-    });
-
-    it('logs a telemetry event when compressing', async () => {
-      vi.spyOn(ClearcutLogger.prototype, 'logChatCompressionEvent');
-      const MOCKED_TOKEN_LIMIT = 1000;
-      const MOCKED_CONTEXT_PERCENTAGE_THRESHOLD = 0.5;
-      vi.spyOn(client['config'], 'getChatCompression').mockReturnValue({
-        contextPercentageThreshold: MOCKED_CONTEXT_PERCENTAGE_THRESHOLD,
-      });
-      const history = [
-        { role: 'user', parts: [{ text: '...history...' }] },
-        { role: 'model', parts: [{ text: '...history...' }] },
-        { role: 'user', parts: [{ text: '...history...' }] },
-        { role: 'model', parts: [{ text: '...history...' }] },
-        { role: 'user', parts: [{ text: '...history...' }] },
-        { role: 'model', parts: [{ text: '...history...' }] },
-      ];
-      mockGetHistory.mockReturnValue(history);
-
-      const originalTokenCount =
-        MOCKED_TOKEN_LIMIT * MOCKED_CONTEXT_PERCENTAGE_THRESHOLD;
-
-      vi.mocked(uiTelemetryService.getLastPromptTokenCount).mockReturnValue(
-        originalTokenCount,
-      );
-
-      // We need to control the estimated new token count.
-      // We mock startChat to return a chat with a known history.
-      const summaryText = 'This is a summary.';
-      const splitPoint = findCompressSplitPoint(history, 0.7);
-      const historyToKeep = history.slice(splitPoint);
-      const newCompressedHistory: Content[] = [
-        { role: 'user', parts: [{ text: 'Mocked env context' }] },
-        { role: 'model', parts: [{ text: 'Got it. Thanks for the context!' }] },
-        { role: 'user', parts: [{ text: summaryText }] },
-        {
-          role: 'model',
-          parts: [{ text: 'Got it. Thanks for the additional context!' }],
-        },
-        ...historyToKeep,
-      ];
-      const mockNewChat: Partial<GeminiChat> = {
-        getHistory: vi.fn().mockReturnValue(newCompressedHistory),
-      };
-      client['startChat'] = vi
-        .fn()
-        .mockResolvedValue(mockNewChat as GeminiChat);
-
-      const totalChars = newCompressedHistory.reduce(
-        (total, content) => total + JSON.stringify(content).length,
-        0,
-      );
-      const newTokenCount = Math.floor(totalChars / 4);
-
-      // Mock the summary response from the chat
-      mockGenerateContentFn.mockResolvedValue({
-        candidates: [
-          {
-            content: {
-              role: 'model',
-              parts: [{ text: summaryText }],
-            },
-          },
-        ],
-      } as unknown as GenerateContentResponse);
-
-      await client.tryCompressChat('prompt-id-3', false);
-
-      expect(
-        ClearcutLogger.prototype.logChatCompressionEvent,
-      ).toHaveBeenCalledWith(
-        expect.objectContaining({
-          tokens_before: originalTokenCount,
-          tokens_after: newTokenCount,
-        }),
-      );
-      expect(uiTelemetryService.setLastPromptTokenCount).toHaveBeenCalledWith(
-        newTokenCount,
-      );
-      expect(uiTelemetryService.setLastPromptTokenCount).toHaveBeenCalledTimes(
-        1,
-      );
-    });
-
-    it('should trigger summarization if token count is at threshold with contextPercentageThreshold setting', async () => {
-      const MOCKED_TOKEN_LIMIT = 1000;
-      const MOCKED_CONTEXT_PERCENTAGE_THRESHOLD = 0.5;
-      vi.mocked(tokenLimit).mockReturnValue(MOCKED_TOKEN_LIMIT);
-      vi.spyOn(client['config'], 'getChatCompression').mockReturnValue({
-        contextPercentageThreshold: MOCKED_CONTEXT_PERCENTAGE_THRESHOLD,
-      });
-      const history = [
-        { role: 'user', parts: [{ text: '...history...' }] },
-        { role: 'model', parts: [{ text: '...history...' }] },
-        { role: 'user', parts: [{ text: '...history...' }] },
-        { role: 'model', parts: [{ text: '...history...' }] },
-        { role: 'user', parts: [{ text: '...history...' }] },
-        { role: 'model', parts: [{ text: '...history...' }] },
-      ];
-      mockGetHistory.mockReturnValue(history);
-
-      const originalTokenCount =
-        MOCKED_TOKEN_LIMIT * MOCKED_CONTEXT_PERCENTAGE_THRESHOLD;
-
-      vi.mocked(uiTelemetryService.getLastPromptTokenCount).mockReturnValue(
-        originalTokenCount,
-      );
-
-      // Mock summary and new chat
-      const summaryText = 'This is a summary.';
-      const splitPoint = findCompressSplitPoint(history, 0.7);
-      const historyToKeep = history.slice(splitPoint);
-      const newCompressedHistory: Content[] = [
-        { role: 'user', parts: [{ text: 'Mocked env context' }] },
-        { role: 'model', parts: [{ text: 'Got it. Thanks for the context!' }] },
-        { role: 'user', parts: [{ text: summaryText }] },
-        {
-          role: 'model',
-          parts: [{ text: 'Got it. Thanks for the additional context!' }],
-        },
-        ...historyToKeep,
-      ];
-      const mockNewChat: Partial<GeminiChat> = {
-        getHistory: vi.fn().mockReturnValue(newCompressedHistory),
-      };
-      client['startChat'] = vi
-        .fn()
-        .mockResolvedValue(mockNewChat as GeminiChat);
-
-      const totalChars = newCompressedHistory.reduce(
-        (total, content) => total + JSON.stringify(content).length,
-        0,
-      );
-      const newTokenCount = Math.floor(totalChars / 4);
-
-      // Mock the summary response from the chat
-      mockGenerateContentFn.mockResolvedValue({
-        candidates: [
-          {
-            content: {
-              role: 'model',
-              parts: [{ text: summaryText }],
-            },
-          },
-        ],
-      } as unknown as GenerateContentResponse);
-
-      const initialChat = client.getChat();
-      const result = await client.tryCompressChat('prompt-id-3', false);
-      const newChat = client.getChat();
-
-      expect(tokenLimit).toHaveBeenCalled();
-      expect(mockGenerateContentFn).toHaveBeenCalled();
-
-      // Assert that summarization happened and returned the correct stats
-      expect(result).toEqual({
-        compressionStatus: CompressionStatus.COMPRESSED,
-        originalTokenCount,
-        newTokenCount,
-      });
-
-      // Assert that the chat was reset
-      expect(newChat).not.toBe(initialChat);
-    });
-
-    it('should not compress across a function call response', async () => {
-      const MOCKED_TOKEN_LIMIT = 1000;
-      vi.mocked(tokenLimit).mockReturnValue(MOCKED_TOKEN_LIMIT);
-      const history: Content[] = [
-        { role: 'user', parts: [{ text: '...history 1...' }] },
-        { role: 'model', parts: [{ text: '...history 2...' }] },
-        { role: 'user', parts: [{ text: '...history 3...' }] },
-        { role: 'model', parts: [{ text: '...history 4...' }] },
-        { role: 'user', parts: [{ text: '...history 5...' }] },
-        { role: 'model', parts: [{ text: '...history 6...' }] },
-        { role: 'user', parts: [{ text: '...history 7...' }] },
-        { role: 'model', parts: [{ text: '...history 8...' }] },
-        // Normally we would break here, but we have a function response.
-        {
-          role: 'user',
-          parts: [{ functionResponse: { name: '...history 8...' } }],
-        },
-        { role: 'model', parts: [{ text: '...history 10...' }] },
-        // Instead we will break here.
-        { role: 'user', parts: [{ text: '...history 10...' }] },
-      ];
-      mockGetHistory.mockReturnValue(history);
-
-      const originalTokenCount = 1000 * 0.7;
-      vi.mocked(uiTelemetryService.getLastPromptTokenCount).mockReturnValue(
-        originalTokenCount,
-      );
-
-      // Mock summary and new chat
-      const summaryText = 'This is a summary.';
-      const splitPoint = findCompressSplitPoint(history, 0.7); // This should be 10
-      expect(splitPoint).toBe(10); // Verify split point logic
-      const historyToKeep = history.slice(splitPoint); // Should keep last user message
-      expect(historyToKeep).toEqual([
-        { role: 'user', parts: [{ text: '...history 10...' }] },
-      ]);
-
-      const newCompressedHistory: Content[] = [
-        { role: 'user', parts: [{ text: 'Mocked env context' }] },
-        { role: 'model', parts: [{ text: 'Got it. Thanks for the context!' }] },
-        { role: 'user', parts: [{ text: summaryText }] },
-        {
-          role: 'model',
-          parts: [{ text: 'Got it. Thanks for the additional context!' }],
-        },
-        ...historyToKeep,
-      ];
-      const mockNewChat: Partial<GeminiChat> = {
-        getHistory: vi.fn().mockReturnValue(newCompressedHistory),
-      };
-      client['startChat'] = vi
-        .fn()
-        .mockResolvedValue(mockNewChat as GeminiChat);
-
-      const totalChars = newCompressedHistory.reduce(
-        (total, content) => total + JSON.stringify(content).length,
-        0,
-      );
-      const newTokenCount = Math.floor(totalChars / 4);
-
-      // Mock the summary response from the chat
-      mockGenerateContentFn.mockResolvedValue({
-        candidates: [
-          {
-            content: {
-              role: 'model',
-              parts: [{ text: summaryText }],
-            },
-          },
-        ],
-      } as unknown as GenerateContentResponse);
-
-      const initialChat = client.getChat();
-      const result = await client.tryCompressChat('prompt-id-3', false);
-      const newChat = client.getChat();
-
-      expect(tokenLimit).toHaveBeenCalled();
-      expect(mockGenerateContentFn).toHaveBeenCalled();
-
-      // Assert that summarization happened and returned the correct stats
-      expect(result).toEqual({
-        compressionStatus: CompressionStatus.COMPRESSED,
-        originalTokenCount,
-        newTokenCount,
-      });
-      // Assert that the chat was reset
-      expect(newChat).not.toBe(initialChat);
-
-      // 1. standard start context message (env)
-      // 2. standard canned model response
-      // 3. compressed summary message (user)
-      // 4. standard canned model response
-      // 5. The last user message (historyToKeep)
-      expect(newChat.getHistory().length).toEqual(5);
-    });
-
-    it('should always trigger summarization when force is true, regardless of token count', async () => {
-      const history = [
-        { role: 'user', parts: [{ text: '...history...' }] },
-        { role: 'model', parts: [{ text: '...history...' }] },
-        { role: 'user', parts: [{ text: '...history...' }] },
-        { role: 'model', parts: [{ text: '...history...' }] },
-        { role: 'user', parts: [{ text: '...history...' }] },
-        { role: 'model', parts: [{ text: '...history...' }] },
-      ];
-      mockGetHistory.mockReturnValue(history);
-
-      const originalTokenCount = 100; // Well below threshold, but > estimated new count
-      vi.mocked(uiTelemetryService.getLastPromptTokenCount).mockReturnValue(
-        originalTokenCount,
-      );
-
-      // Mock summary and new chat
-      const summaryText = 'This is a summary.';
-      const splitPoint = findCompressSplitPoint(history, 0.7);
-      const historyToKeep = history.slice(splitPoint);
-      const newCompressedHistory: Content[] = [
-        { role: 'user', parts: [{ text: 'Mocked env context' }] },
-        { role: 'model', parts: [{ text: 'Got it. Thanks for the context!' }] },
-        { role: 'user', parts: [{ text: summaryText }] },
-        {
-          role: 'model',
-          parts: [{ text: 'Got it. Thanks for the additional context!' }],
-        },
-        ...historyToKeep,
-      ];
-      const mockNewChat: Partial<GeminiChat> = {
-        getHistory: vi.fn().mockReturnValue(newCompressedHistory),
-      };
-      client['startChat'] = vi
-        .fn()
-        .mockResolvedValue(mockNewChat as GeminiChat);
-
-      const totalChars = newCompressedHistory.reduce(
-        (total, content) => total + JSON.stringify(content).length,
-        0,
-      );
-      const newTokenCount = Math.floor(totalChars / 4);
-
-      // Mock the summary response from the chat
-      mockGenerateContentFn.mockResolvedValue({
-        candidates: [
-          {
-            content: {
-              role: 'model',
-              parts: [{ text: summaryText }],
-            },
-          },
-        ],
-      } as unknown as GenerateContentResponse);
-
-      const initialChat = client.getChat();
-      const result = await client.tryCompressChat('prompt-id-1', true); // force = true
-      const newChat = client.getChat();
-
-      expect(mockGenerateContentFn).toHaveBeenCalled();
-
-      expect(result).toEqual({
-        compressionStatus: CompressionStatus.COMPRESSED,
-        originalTokenCount,
-        newTokenCount,
-      });
-
-      // Assert that the chat was reset
-      expect(newChat).not.toBe(initialChat);
    });
  });

@@ -2073,7 +1669,11 @@ ${JSON.stringify(
          vi.mocked(ideContextStore.get).mockReturnValue({
            workspaceState: {
              openFiles: [
-                { ...currentActiveFile, isActive: true, timestamp: Date.now() },
+                {
+                  ...currentActiveFile,
+                  isActive: true,
+                  timestamp: Date.now(),
+                },
              ],
            },
          });
@@ -13,14 +13,13 @@ import type {
 } from '@google/genai';
 import {
  getDirectoryContextString,
-  getEnvironmentContext,
+  getInitialChatHistory,
 } from '../utils/environmentContext.js';
 import type { ServerGeminiStreamEvent, ChatCompressionInfo } from './turn.js';
 import { CompressionStatus } from './turn.js';
 import { Turn, GeminiEventType } from './turn.js';
 import type { Config } from '../config/config.js';
-import { getCoreSystemPrompt, getCompressionPrompt } from './prompts.js';
-import { getResponseText } from '../utils/partUtils.js';
+import { getCoreSystemPrompt } from './prompts.js';
 import { checkNextSpeaker } from '../utils/nextSpeakerChecker.js';
 import { reportError } from '../utils/errorReporting.js';
 import { GeminiChat } from './geminiChat.js';
@@ -37,15 +36,14 @@ import {
  getEffectiveModel,
 } from '../config/models.js';
 import { LoopDetectionService } from '../services/loopDetectionService.js';
+import { ChatCompressionService } from '../services/chatCompressionService.js';
 import { ideContextStore } from '../ide/ideContext.js';
 import {
-  logChatCompression,
  logContentRetryFailure,
  logNextSpeakerCheck,
 } from '../telemetry/loggers.js';
 import {
  ContentRetryFailureEvent,
-  makeChatCompressionEvent,
  NextSpeakerCheckEvent,
 } from '../telemetry/types.js';
 import type { IdeContext, File } from '../ide/types.js';
@@ -65,68 +63,8 @@ export function isThinkingDefault(model: string) {
  return model.startsWith('gemini-2.5') || model === DEFAULT_GEMINI_MODEL_AUTO;
 }

-/**
- * Returns the index of the oldest item to keep when compressing. May return
- * contents.length which indicates that everything should be compressed.
- *
- * Exported for testing purposes.
- */
-export function findCompressSplitPoint(
-  contents: Content[],
-  fraction: number,
-): number {
-  if (fraction <= 0 || fraction >= 1) {
-    throw new Error('Fraction must be between 0 and 1');
-  }
-
-  const charCounts = contents.map((content) => JSON.stringify(content).length);
-  const totalCharCount = charCounts.reduce((a, b) => a + b, 0);
-  const targetCharCount = totalCharCount * fraction;
-
-  let lastSplitPoint = 0; // 0 is always valid (compress nothing)
-  let cumulativeCharCount = 0;
-  for (let i = 0; i < contents.length; i++) {
-    const content = contents[i];
-    if (
-      content.role === 'user' &&
-      !content.parts?.some((part) => !!part.functionResponse)
-    ) {
-      if (cumulativeCharCount >= targetCharCount) {
-        return i;
-      }
-      lastSplitPoint = i;
-    }
-    cumulativeCharCount += charCounts[i];
-  }
-
-  // We found no split points after targetCharCount.
-  // Check if it's safe to compress everything.
-  const lastContent = contents[contents.length - 1];
-  if (
-    lastContent?.role === 'model' &&
-    !lastContent?.parts?.some((part) => part.functionCall)
-  ) {
-    return contents.length;
-  }
-
-  // Can't compress everything so just compress at last splitpoint.
-  return lastSplitPoint;
-}
-
 const MAX_TURNS = 100;

-/**
- * Threshold for compression token count as a fraction of the model's token limit.
- * If the chat history exceeds this threshold, it will be compressed.
- */
-const COMPRESSION_TOKEN_THRESHOLD = 0.7;
-
-/**
- * The fraction of the latest chat history to keep. A value of 0.3
- * means that only the last 30% of the chat history will be kept after compression.
- */
-const COMPRESSION_PRESERVE_THRESHOLD = 0.3;
-
 export class GeminiClient {
  private chat?: GeminiChat;
  private readonly generateContentConfig: GenerateContentConfig = {
@@ -136,6 +74,7 @@ export class GeminiClient {
  private sessionTurnCount = 0;

  private readonly loopDetector: LoopDetectionService;
+  private readonly compressionService: ChatCompressionService;
  private lastPromptId: string;
  private currentSequenceModel: string | null = null;
  private lastSentIdeContext: IdeContext | undefined;
@@ -149,6 +88,7 @@ export class GeminiClient {

  constructor(private readonly config: Config) {
    this.loopDetector = new LoopDetectionService(config);
+    this.compressionService = new ChatCompressionService();
    this.lastPromptId = this.config.getSessionId();
  }

@@ -233,31 +173,7 @@ export class GeminiClient {
    const toolDeclarations = toolRegistry.getFunctionDeclarations();
    const tools: Tool[] = [{ functionDeclarations: toolDeclarations }];

-    // 1. Get the environment context parts as an array
-    const envParts = await getEnvironmentContext(this.config);
-
-    // 2. Convert the array of parts into a single string
-    const envContextString = envParts
-      .map((part) => part.text || '')
-      .join('\n\n');
-
-    // 3. Combine the dynamic context with the static handshake instruction
-    const allSetupText = `
-${envContextString}
-
-Reminder: Do not return an empty response when a tool call is required.
-
-My setup is complete. I will provide my first command in the next turn.
-    `.trim();
-
-    // 4. Create the history with a single, comprehensive user turn
-    const history: Content[] = [
-      {
-        role: 'user',
-        parts: [{ text: allSetupText }],
-      },
-      ...(extraHistory ?? []),
-    ];
+    const history = await getInitialChatHistory(this.config, extraHistory);

    try {
      const userMemory = this.config.getUserMemory();
@@ -738,129 +654,27 @@ My setup is complete. I will provide my first command in the next turn.
    // before the model is chosen would result in an error.
    const model = this._getEffectiveModelForCurrentTurn();

-    const curatedHistory = this.getChat().getHistory(true);
+    const { newHistory, info } = await this.compressionService.compress(
+      this.getChat(),
+      prompt_id,
+      force,
+      model,
+      this.config,
+      this.hasFailedCompressionAttempt,
+    );

-    // Regardless of `force`, don't do anything if the history is empty.
    if (
-      curatedHistory.length === 0 ||
-      (this.hasFailedCompressionAttempt && !force)
+      info.compressionStatus ===
+      CompressionStatus.COMPRESSION_FAILED_INFLATED_TOKEN_COUNT
    ) {
-      return {
-        originalTokenCount: 0,
-        newTokenCount: 0,
-        compressionStatus: CompressionStatus.NOOP,
-      };
-    }
-
-    const originalTokenCount = uiTelemetryService.getLastPromptTokenCount();
-
-    const contextPercentageThreshold =
-      this.config.getChatCompression()?.contextPercentageThreshold;
-
-    // Don't compress if not forced and we are under the limit.
-    if (!force) {
-      const threshold =
-        contextPercentageThreshold ?? COMPRESSION_TOKEN_THRESHOLD;
-      if (originalTokenCount < threshold * tokenLimit(model)) {
-        return {
-          originalTokenCount,
-          newTokenCount: originalTokenCount,
-          compressionStatus: CompressionStatus.NOOP,
-        };
+      this.hasFailedCompressionAttempt = !force && true;
+    } else if (info.compressionStatus === CompressionStatus.COMPRESSED) {
+      if (newHistory) {
+        this.chat = await this.startChat(newHistory);
+        this.forceFullIdeContext = true;
      }
    }

-    const splitPoint = findCompressSplitPoint(
-      curatedHistory,
-      1 - COMPRESSION_PRESERVE_THRESHOLD,
-    );
-
-    const historyToCompress = curatedHistory.slice(0, splitPoint);
-    const historyToKeep = curatedHistory.slice(splitPoint);
-
-    if (historyToCompress.length === 0) {
-      return {
-        originalTokenCount,
-        newTokenCount: originalTokenCount,
-        compressionStatus: CompressionStatus.NOOP,
-      };
-    }
-
-    const summaryResponse = await this.config
-      .getContentGenerator()
-      .generateContent(
-        {
-          model,
-          contents: [
-            ...historyToCompress,
-            {
-              role: 'user',
-              parts: [
-                {
-                  text: 'First, reason in your scratchpad. Then, generate the <state_snapshot>.',
-                },
-              ],
-            },
-          ],
-          config: {
-            systemInstruction: { text: getCompressionPrompt() },
-          },
-        },
-        prompt_id,
-      );
-    const summary = getResponseText(summaryResponse) ?? '';
-
-    const chat = await this.startChat([
-      {
-        role: 'user',
-        parts: [{ text: summary }],
-      },
-      {
-        role: 'model',
-        parts: [{ text: 'Got it. Thanks for the additional context!' }],
-      },
-      ...historyToKeep,
-    ]);
-    this.forceFullIdeContext = true;
-
-    // Estimate token count 1 token ≈ 4 characters
-    const newTokenCount = Math.floor(
-      chat
-        .getHistory()
-        .reduce((total, content) => total + JSON.stringify(content).length, 0) /
-        4,
-    );
-
-    logChatCompression(
-      this.config,
-      makeChatCompressionEvent({
-        tokens_before: originalTokenCount,
-        tokens_after: newTokenCount,
-      }),
-    );
-
-    if (newTokenCount > originalTokenCount) {
-      this.hasFailedCompressionAttempt = !force && true;
-      return {
-        originalTokenCount,
-        newTokenCount,
-        compressionStatus:
-          CompressionStatus.COMPRESSION_FAILED_INFLATED_TOKEN_COUNT,
-      };
-    } else {
-      this.chat = chat; // Chat compression successful, set new state.
-      uiTelemetryService.setLastPromptTokenCount(newTokenCount);
-    }
-
-    return {
-      originalTokenCount,
-      newTokenCount,
-      compressionStatus: CompressionStatus.COMPRESSED,
-    };
+    return info;
  }
 }
-
-export const TEST_ONLY = {
-  COMPRESSION_PRESERVE_THRESHOLD,
-  COMPRESSION_TOKEN_THRESHOLD,
-};
@@ -0,0 +1,296 @@
+/**
+ * @license
+ * Copyright 2025 Google LLC
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+import { describe, it, expect, vi, beforeEach, afterEach } from 'vitest';
+import {
+  ChatCompressionService,
+  findCompressSplitPoint,
+} from './chatCompressionService.js';
+import type { Content, GenerateContentResponse } from '@google/genai';
+import { CompressionStatus } from '../core/turn.js';
+import { uiTelemetryService } from '../telemetry/uiTelemetry.js';
+import { tokenLimit } from '../core/tokenLimits.js';
+import type { GeminiChat } from '../core/geminiChat.js';
+import type { Config } from '../config/config.js';
+import { getInitialChatHistory } from '../utils/environmentContext.js';
+import type { ContentGenerator } from '../core/contentGenerator.js';
+
+vi.mock('../telemetry/uiTelemetry.js');
+vi.mock('../core/tokenLimits.js');
+vi.mock('../telemetry/loggers.js');
+vi.mock('../utils/environmentContext.js');
+
+describe('findCompressSplitPoint', () => {
+  it('should throw an error for non-positive numbers', () => {
+    expect(() => findCompressSplitPoint([], 0)).toThrow(
+      'Fraction must be between 0 and 1',
+    );
+  });
+
+  it('should throw an error for a fraction greater than or equal to 1', () => {
+    expect(() => findCompressSplitPoint([], 1)).toThrow(
+      'Fraction must be between 0 and 1',
+    );
+  });
+
+  it('should handle an empty history', () => {
+    expect(findCompressSplitPoint([], 0.5)).toBe(0);
+  });
+
+  it('should handle a fraction in the middle', () => {
+    const history: Content[] = [
+      { role: 'user', parts: [{ text: 'This is the first message.' }] }, // JSON length: 66 (19%)
+      { role: 'model', parts: [{ text: 'This is the second message.' }] }, // JSON length: 68 (40%)
+      { role: 'user', parts: [{ text: 'This is the third message.' }] }, // JSON length: 66 (60%)
+      { role: 'model', parts: [{ text: 'This is the fourth message.' }] }, // JSON length: 68 (80%)
+      { role: 'user', parts: [{ text: 'This is the fifth message.' }] }, // JSON length: 65 (100%)
+    ];
+    expect(findCompressSplitPoint(history, 0.5)).toBe(4);
+  });
+
+  it('should handle a fraction of last index', () => {
+    const history: Content[] = [
+      { role: 'user', parts: [{ text: 'This is the first message.' }] }, // JSON length: 66 (19%)
+      { role: 'model', parts: [{ text: 'This is the second message.' }] }, // JSON length: 68 (40%)
+      { role: 'user', parts: [{ text: 'This is the third message.' }] }, // JSON length: 66 (60%)
+      { role: 'model', parts: [{ text: 'This is the fourth message.' }] }, // JSON length: 68 (80%)
+      { role: 'user', parts: [{ text: 'This is the fifth message.' }] }, // JSON length: 65 (100%)
+    ];
+    expect(findCompressSplitPoint(history, 0.9)).toBe(4);
+  });
+
+  it('should handle a fraction of after last index', () => {
+    const history: Content[] = [
+      { role: 'user', parts: [{ text: 'This is the first message.' }] }, // JSON length: 66 (24%)
+      { role: 'model', parts: [{ text: 'This is the second message.' }] }, // JSON length: 68 (50%)
+      { role: 'user', parts: [{ text: 'This is the third message.' }] }, // JSON length: 66 (74%)
+      { role: 'model', parts: [{ text: 'This is the fourth message.' }] }, // JSON length: 68 (100%)
+    ];
+    expect(findCompressSplitPoint(history, 0.8)).toBe(4);
+  });
+
+  it('should return earlier splitpoint if no valid ones are after threshold', () => {
+    const history: Content[] = [
+      { role: 'user', parts: [{ text: 'This is the first message.' }] },
+      { role: 'model', parts: [{ text: 'This is the second message.' }] },
+      { role: 'user', parts: [{ text: 'This is the third message.' }] },
+      { role: 'model', parts: [{ functionCall: { name: 'foo', args: {} } }] },
+    ];
+    // Can't return 4 because the previous item has a function call.
+    expect(findCompressSplitPoint(history, 0.99)).toBe(2);
+  });
+
+  it('should handle a history with only one item', () => {
+    const historyWithEmptyParts: Content[] = [
+      { role: 'user', parts: [{ text: 'Message 1' }] },
+    ];
+    expect(findCompressSplitPoint(historyWithEmptyParts, 0.5)).toBe(0);
+  });
+
+  it('should handle history with weird parts', () => {
+    const historyWithEmptyParts: Content[] = [
+      { role: 'user', parts: [{ text: 'Message 1' }] },
+      {
+        role: 'model',
+        parts: [{ fileData: { fileUri: 'derp', mimeType: 'text/plain' } }],
+      },
+      { role: 'user', parts: [{ text: 'Message 2' }] },
+    ];
+    expect(findCompressSplitPoint(historyWithEmptyParts, 0.5)).toBe(2);
+  });
+});
+
+describe('ChatCompressionService', () => {
+  let service: ChatCompressionService;
+  let mockChat: GeminiChat;
+  let mockConfig: Config;
+  const mockModel = 'gemini-pro';
+  const mockPromptId = 'test-prompt-id';
+
+  beforeEach(() => {
+    service = new ChatCompressionService();
+    mockChat = {
+      getHistory: vi.fn(),
+    } as unknown as GeminiChat;
+    mockConfig = {
+      getCompressionThreshold: vi.fn(),
+      getContentGenerator: vi.fn(),
+    } as unknown as Config;
+
+    vi.mocked(tokenLimit).mockReturnValue(1000);
+    vi.mocked(uiTelemetryService.getLastPromptTokenCount).mockReturnValue(500);
+    vi.mocked(getInitialChatHistory).mockImplementation(
+      async (_config, extraHistory) => extraHistory || [],
+    );
+  });
+
+  afterEach(() => {
+    vi.restoreAllMocks();
+  });
+
+  it('should return NOOP if history is empty', async () => {
+    vi.mocked(mockChat.getHistory).mockReturnValue([]);
+    const result = await service.compress(
+      mockChat,
+      mockPromptId,
+      false,
+      mockModel,
+      mockConfig,
+      false,
+    );
+    expect(result.info.compressionStatus).toBe(CompressionStatus.NOOP);
+    expect(result.newHistory).toBeNull();
+  });
+
+  it('should return NOOP if previously failed and not forced', async () => {
+    vi.mocked(mockChat.getHistory).mockReturnValue([
+      { role: 'user', parts: [{ text: 'hi' }] },
+    ]);
+    const result = await service.compress(
+      mockChat,
+      mockPromptId,
+      false,
+      mockModel,
+      mockConfig,
+      true,
+    );
+    expect(result.info.compressionStatus).toBe(CompressionStatus.NOOP);
+    expect(result.newHistory).toBeNull();
+  });
+
+  it('should return NOOP if under token threshold and not forced', async () => {
+    vi.mocked(mockChat.getHistory).mockReturnValue([
+      { role: 'user', parts: [{ text: 'hi' }] },
+    ]);
+    vi.mocked(uiTelemetryService.getLastPromptTokenCount).mockReturnValue(600);
+    vi.mocked(tokenLimit).mockReturnValue(1000);
+    // Threshold is 0.7 * 1000 = 700. 600 < 700, so NOOP.
+
+    const result = await service.compress(
+      mockChat,
+      mockPromptId,
+      false,
+      mockModel,
+      mockConfig,
+      false,
+    );
+    expect(result.info.compressionStatus).toBe(CompressionStatus.NOOP);
+    expect(result.newHistory).toBeNull();
+  });
+
+  it('should compress if over token threshold', async () => {
+    const history: Content[] = [
+      { role: 'user', parts: [{ text: 'msg1' }] },
+      { role: 'model', parts: [{ text: 'msg2' }] },
+      { role: 'user', parts: [{ text: 'msg3' }] },
+      { role: 'model', parts: [{ text: 'msg4' }] },
+    ];
+    vi.mocked(mockChat.getHistory).mockReturnValue(history);
+    vi.mocked(uiTelemetryService.getLastPromptTokenCount).mockReturnValue(800);
+    vi.mocked(tokenLimit).mockReturnValue(1000);
+    const mockGenerateContent = vi.fn().mockResolvedValue({
+      candidates: [
+        {
+          content: {
+            parts: [{ text: 'Summary' }],
+          },
+        },
+      ],
+    } as unknown as GenerateContentResponse);
+    vi.mocked(mockConfig.getContentGenerator).mockReturnValue({
+      generateContent: mockGenerateContent,
+    } as unknown as ContentGenerator);
+
+    const result = await service.compress(
+      mockChat,
+      mockPromptId,
+      false,
+      mockModel,
+      mockConfig,
+      false,
+    );
+
+    expect(result.info.compressionStatus).toBe(CompressionStatus.COMPRESSED);
+    expect(result.newHistory).not.toBeNull();
+    expect(result.newHistory![0].parts![0].text).toBe('Summary');
+    expect(mockGenerateContent).toHaveBeenCalled();
+  });
+
+  it('should force compress even if under threshold', async () => {
+    const history: Content[] = [
+      { role: 'user', parts: [{ text: 'msg1' }] },
+      { role: 'model', parts: [{ text: 'msg2' }] },
+      { role: 'user', parts: [{ text: 'msg3' }] },
+      { role: 'model', parts: [{ text: 'msg4' }] },
+    ];
+    vi.mocked(mockChat.getHistory).mockReturnValue(history);
+    vi.mocked(uiTelemetryService.getLastPromptTokenCount).mockReturnValue(100);
+    vi.mocked(tokenLimit).mockReturnValue(1000);
+
+    const mockGenerateContent = vi.fn().mockResolvedValue({
+      candidates: [
+        {
+          content: {
+            parts: [{ text: 'Summary' }],
+          },
+        },
+      ],
+    } as unknown as GenerateContentResponse);
+    vi.mocked(mockConfig.getContentGenerator).mockReturnValue({
+      generateContent: mockGenerateContent,
+    } as unknown as ContentGenerator);
+
+    const result = await service.compress(
+      mockChat,
+      mockPromptId,
+      true, // forced
+      mockModel,
+      mockConfig,
+      false,
+    );
+
+    expect(result.info.compressionStatus).toBe(CompressionStatus.COMPRESSED);
+    expect(result.newHistory).not.toBeNull();
+  });
+
+  it('should return FAILED if new token count is inflated', async () => {
+    const history: Content[] = [
+      { role: 'user', parts: [{ text: 'msg1' }] },
+      { role: 'model', parts: [{ text: 'msg2' }] },
+    ];
+    vi.mocked(mockChat.getHistory).mockReturnValue(history);
+    vi.mocked(uiTelemetryService.getLastPromptTokenCount).mockReturnValue(10);
+    vi.mocked(tokenLimit).mockReturnValue(1000);
+
+    const longSummary = 'a'.repeat(1000); // Long summary to inflate token count
+    const mockGenerateContent = vi.fn().mockResolvedValue({
+      candidates: [
+        {
+          content: {
+            parts: [{ text: longSummary }],
+          },
+        },
+      ],
+    } as unknown as GenerateContentResponse);
+    vi.mocked(mockConfig.getContentGenerator).mockReturnValue({
+      generateContent: mockGenerateContent,
+    } as unknown as ContentGenerator);
+
+    const result = await service.compress(
+      mockChat,
+      mockPromptId,
+      true,
+      mockModel,
+      mockConfig,
+      false,
+    );
+
+    expect(result.info.compressionStatus).toBe(
+      CompressionStatus.COMPRESSION_FAILED_INFLATED_TOKEN_COUNT,
+    );
+    expect(result.newHistory).toBeNull();
+  });
+});
@@ -0,0 +1,217 @@
+/**
+ * @license
+ * Copyright 2025 Google LLC
+ * SPDX-License-Identifier: Apache-2.0
+ */
+
+import type { Content } from '@google/genai';
+import type { Config } from '../config/config.js';
+import type { GeminiChat } from '../core/geminiChat.js';
+import { type ChatCompressionInfo, CompressionStatus } from '../core/turn.js';
+import { uiTelemetryService } from '../telemetry/uiTelemetry.js';
+import { tokenLimit } from '../core/tokenLimits.js';
+import { getCompressionPrompt } from '../core/prompts.js';
+import { getResponseText } from '../utils/partUtils.js';
+import { logChatCompression } from '../telemetry/loggers.js';
+import { makeChatCompressionEvent } from '../telemetry/types.js';
+import { getInitialChatHistory } from '../utils/environmentContext.js';
+
+/**
+ * Default threshold for compression token count as a fraction of the model's
+ * token limit. If the chat history exceeds this threshold, it will be compressed.
+ */
+export const DEFAULT_COMPRESSION_TOKEN_THRESHOLD = 0.2;
+
+/**
+ * The fraction of the latest chat history to keep. A value of 0.3
+ * means that only the last 30% of the chat history will be kept after compression.
+ */
+export const COMPRESSION_PRESERVE_THRESHOLD = 0.3;
+
+/**
+ * Returns the index of the oldest item to keep when compressing. May return
+ * contents.length which indicates that everything should be compressed.
+ *
+ * Exported for testing purposes.
+ */
+export function findCompressSplitPoint(
+  contents: Content[],
+  fraction: number,
+): number {
+  if (fraction <= 0 || fraction >= 1) {
+    throw new Error('Fraction must be between 0 and 1');
+  }
+
+  const charCounts = contents.map((content) => JSON.stringify(content).length);
+  const totalCharCount = charCounts.reduce((a, b) => a + b, 0);
+  const targetCharCount = totalCharCount * fraction;
+
+  let lastSplitPoint = 0; // 0 is always valid (compress nothing)
+  let cumulativeCharCount = 0;
+  for (let i = 0; i < contents.length; i++) {
+    const content = contents[i];
+    if (
+      content.role === 'user' &&
+      !content.parts?.some((part) => !!part.functionResponse)
+    ) {
+      if (cumulativeCharCount >= targetCharCount) {
+        return i;
+      }
+      lastSplitPoint = i;
+    }
+    cumulativeCharCount += charCounts[i];
+  }
+
+  // We found no split points after targetCharCount.
+  // Check if it's safe to compress everything.
+  const lastContent = contents[contents.length - 1];
+  if (
+    lastContent?.role === 'model' &&
+    !lastContent?.parts?.some((part) => part.functionCall)
+  ) {
+    return contents.length;
+  }
+
+  // Can't compress everything so just compress at last splitpoint.
+  return lastSplitPoint;
+}
+
+export class ChatCompressionService {
+  async compress(
+    chat: GeminiChat,
+    promptId: string,
+    force: boolean,
+    model: string,
+    config: Config,
+    hasFailedCompressionAttempt: boolean,
+  ): Promise<{ newHistory: Content[] | null; info: ChatCompressionInfo }> {
+    const curatedHistory = chat.getHistory(true);
+
+    // Regardless of `force`, don't do anything if the history is empty.
+    if (
+      curatedHistory.length === 0 ||
+      (hasFailedCompressionAttempt && !force)
+    ) {
+      return {
+        newHistory: null,
+        info: {
+          originalTokenCount: 0,
+          newTokenCount: 0,
+          compressionStatus: CompressionStatus.NOOP,
+        },
+      };
+    }
+
+    const originalTokenCount = uiTelemetryService.getLastPromptTokenCount();
+
+    // Don't compress if not forced and we are under the limit.
+    if (!force) {
+      const threshold =
+        config.getCompressionThreshold() ?? DEFAULT_COMPRESSION_TOKEN_THRESHOLD;
+      if (originalTokenCount < threshold * tokenLimit(model)) {
+        return {
+          newHistory: null,
+          info: {
+            originalTokenCount,
+            newTokenCount: originalTokenCount,
+            compressionStatus: CompressionStatus.NOOP,
+          },
+        };
+      }
+    }
+
+    const splitPoint = findCompressSplitPoint(
+      curatedHistory,
+      1 - COMPRESSION_PRESERVE_THRESHOLD,
+    );
+
+    const historyToCompress = curatedHistory.slice(0, splitPoint);
+    const historyToKeep = curatedHistory.slice(splitPoint);
+
+    if (historyToCompress.length === 0) {
+      return {
+        newHistory: null,
+        info: {
+          originalTokenCount,
+          newTokenCount: originalTokenCount,
+          compressionStatus: CompressionStatus.NOOP,
+        },
+      };
+    }
+
+    const summaryResponse = await config.getContentGenerator().generateContent(
+      {
+        model,
+        contents: [
+          ...historyToCompress,
+          {
+            role: 'user',
+            parts: [
+              {
+                text: 'First, reason in your scratchpad. Then, generate the <state_snapshot>.',
+              },
+            ],
+          },
+        ],
+        config: {
+          systemInstruction: { text: getCompressionPrompt() },
+        },
+      },
+      promptId,
+    );
+    const summary = getResponseText(summaryResponse) ?? '';
+
+    const extraHistory: Content[] = [
+      {
+        role: 'user',
+        parts: [{ text: summary }],
+      },
+      {
+        role: 'model',
+        parts: [{ text: 'Got it. Thanks for the additional context!' }],
+      },
+      ...historyToKeep,
+    ];
+
+    // Use a shared utility to construct the initial history for an accurate token count.
+    const fullNewHistory = await getInitialChatHistory(config, extraHistory);
+
+    // Estimate token count 1 token ≈ 4 characters
+    const newTokenCount = Math.floor(
+      fullNewHistory.reduce(
+        (total, content) => total + JSON.stringify(content).length,
+        0,
+      ) / 4,
+    );
+
+    logChatCompression(
+      config,
+      makeChatCompressionEvent({
+        tokens_before: originalTokenCount,
+        tokens_after: newTokenCount,
+      }),
+    );
+
+    if (newTokenCount > originalTokenCount) {
+      return {
+        newHistory: null,
+        info: {
+          originalTokenCount,
+          newTokenCount,
+          compressionStatus:
+            CompressionStatus.COMPRESSION_FAILED_INFLATED_TOKEN_COUNT,
+        },
+      };
+    } else {
+      uiTelemetryService.setLastPromptTokenCount(newTokenCount);
+      return {
+        newHistory: extraHistory,
+        info: {
+          originalTokenCount,
+          newTokenCount,
+          compressionStatus: CompressionStatus.COMPRESSED,
+        },
+      };
+    }
+  }
+}
@@ -142,6 +142,19 @@ describe('LoopDetectionService', () => {
      }
      expect(loggers.logLoopDetected).not.toHaveBeenCalled();
    });
+
+    it('should stop reporting a loop if disabled after detection', () => {
+      const event = createToolCallRequestEvent('testTool', { param: 'value' });
+      for (let i = 0; i < TOOL_CALL_LOOP_THRESHOLD; i++) {
+        service.addAndCheck(event);
+      }
+      expect(service.addAndCheck(event)).toBe(true);
+
+      service.disableForSession();
+
+      // Should now return false even though a loop was previously detected
+      expect(service.addAndCheck(event)).toBe(false);
+    });
  });

  describe('Content Loop Detection', () => {
@@ -123,7 +123,11 @@ export class LoopDetectionService {
   * @returns true if a loop is detected, false otherwise
   */
  addAndCheck(event: ServerGeminiStreamEvent): boolean {
-    if (this.loopDetected || this.disabledForSession) {
+    if (this.disabledForSession) {
+      return false;
+    }
+
+    if (this.loopDetected) {
      return this.loopDetected;
    }

@@ -4,7 +4,7 @@
 * SPDX-License-Identifier: Apache-2.0
 */

-import type { Part } from '@google/genai';
+import type { Part, Content } from '@google/genai';
 import type { Config } from '../config/config.js';
 import { getFolderStructure } from './getFolderStructure.js';

@@ -71,3 +71,27 @@ ${directoryContext}

  return initialParts;
 }
+
+export async function getInitialChatHistory(
+  config: Config,
+  extraHistory?: Content[],
+): Promise<Content[]> {
+  const envParts = await getEnvironmentContext(config);
+  const envContextString = envParts.map((part) => part.text || '').join('\n\n');
+
+  const allSetupText = `
+${envContextString}
+
+Reminder: Do not return an empty response when a tool call is required.
+
+My setup is complete. I will provide my first command in the next turn.
+    `.trim();
+
+  return [
+    {
+      role: 'user',
+      parts: [{ text: allSetupText }],
+    },
+    ...(extraHistory ?? []),
+  ];
+}
@@ -96,7 +96,7 @@ export function classifyGoogleError(error: unknown): unknown {
      const quotaId = violation.quotaId ?? '';
      if (quotaId.includes('PerDay') || quotaId.includes('Daily')) {
        return new TerminalQuotaError(
-          `${googleApiError.message}\nExpected quota reset within 24h.`,
+          `You have exhausted your daily quota on this model.`,
          googleApiError,
        );
      }
@@ -139,7 +139,7 @@ export function classifyGoogleError(error: unknown): unknown {
    const quotaLimit = errorInfo.metadata?.['quota_limit'] ?? '';
    if (quotaLimit.includes('PerDay') || quotaLimit.includes('Daily')) {
      return new TerminalQuotaError(
-        `${googleApiError.message}\nExpected quota reset within 24h.`,
+        `You have exhausted your daily quota on this model.`,
        googleApiError,
      );
    }
@@ -1,6 +1,6 @@
 {
  "name": "@google/gemini-cli-test-utils",
-  "version": "0.11.1",
+  "version": "0.11.3",
  "private": true,
  "main": "src/index.ts",
  "license": "Apache-2.0",
@@ -2,7 +2,7 @@
  "name": "gemini-cli-vscode-ide-companion",
  "displayName": "Gemini CLI Companion",
  "description": "Enable Gemini CLI with direct access to your IDE workspace.",
-  "version": "0.11.1",
+  "version": "0.11.3",
  "publisher": "google",
  "icon": "assets/icon.png",
  "repository": {
Author	SHA1	Message	Date
gemini-cli-robot	e5161610ff	chore(release): v0.11.3	2025-10-31 20:24:24 +00:00
Gaurav Ghosh	44b3c97486	refactor: simplify daily quota error messages	2025-10-31 11:11:19 -07:00
Sandy Tao	b1bbef433d	fix(core): ensure loop detection respects session disable flag (#12347 )	2025-10-31 10:31:04 -07:00
Tommaso Sciortino	8a72585992	Mark `model.compressionThreshold` as requiring a restart (#12378 )	2025-10-31 10:31:03 -07:00
Abhi	73b3211ea7	Remove context percentage in footer by default (#12326 )	2025-10-31 10:31:02 -07:00
Tommaso Sciortino	ce40a6534f	Make compression threshold editable in the UI. (#12317 )	2025-10-31 10:30:34 -07:00
Tommaso Sciortino	5be5575df0	Change default compression threshold (#12306 )	2025-10-31 09:32:34 -07:00
Sandy Tao	847c6e7fd0	refactor(core): extract ChatCompressionService from GeminiClient (#12001 )	2025-10-31 09:21:04 -07:00
gemini-cli-robot	f4f3727936	chore(release): v0.11.2	2025-10-31 02:33:21 +00:00
gemini-cli-robot	f36dec6ad4	fix(patch): cherry-pick `643f2c0` to release/v0.11.1-pr-12300 to patch version v0.11.1 and create version 0.11.2 (#12335 ) Co-authored-by: Victor May <mayvic@google.com>	2025-10-30 19:20:45 -07:00