testing

packages/cli/src/config/config.ts

@@ -882,6 +882,7 @@ export async function loadCliConfig(
     ideMode,
     disableLoopDetection: settings.model?.disableLoopDetection,
     compressionThreshold: settings.model?.compressionThreshold,
+    forceCompressionRetries: settings.model?.forceCompressionRetries,
     folderTrust,
     interactive,
     trustedFolder,

packages/cli/src/config/settingsSchema.ts

@@ -970,6 +970,16 @@ const SETTINGS_SCHEMA = {
         showInDialog: true,
         unit: '%',
       },
+      forceCompressionRetries: {
+        type: 'boolean',
+        label: 'Force Compression Retries',
+        category: 'Model',
+        requiresRestart: true,
+        default: false as boolean,
+        description:
+          'If true, summarization will be retried even if a previous summarization attempt in the session failed. Useful for aggressive compression experiments.',
+        showInDialog: false,
+      },
       disableLoopDetection: {
         type: 'boolean',
         label: 'Disable Loop Detection',

packages/core/src/config/config.ts

@@ -598,6 +598,7 @@ export interface ConfigParameters {
   importFormat?: 'tree' | 'flat';
   discoveryMaxDirs?: number;
   compressionThreshold?: number;
+  forceCompressionRetries?: boolean;
   interactive?: boolean;
   trustedFolder?: boolean;
   useBackgroundColor?: boolean;
@@ -792,6 +793,7 @@ export class Config implements McpContext, AgentLoopContext {
   private readonly importFormat: 'tree' | 'flat';
   private readonly discoveryMaxDirs: number;
   private readonly compressionThreshold: number | undefined;
+  private readonly forceCompressionRetries: boolean;
   /** Public for testing only */
   readonly interactive: boolean;
   private readonly ptyInfo: string;
@@ -1086,6 +1088,7 @@ export class Config implements McpContext, AgentLoopContext {
     this.importFormat = params.importFormat ?? 'tree';
     this.discoveryMaxDirs = params.discoveryMaxDirs ?? 200;
     this.compressionThreshold = params.compressionThreshold;
+    this.forceCompressionRetries = params.forceCompressionRetries ?? false;
     this.interactive = params.interactive ?? false;
     this.ptyInfo = params.ptyInfo ?? 'child_process';
     this.trustedFolder = params.trustedFolder;
@@ -2749,6 +2752,10 @@ export class Config implements McpContext, AgentLoopContext {
     return remoteThreshold;
   }
 
+  getForceCompressionRetries(): boolean {
+    return this.forceCompressionRetries;
+  }
+
   async getUserCaching(): Promise<boolean | undefined> {
     await this.ensureExperimentsLoaded();
 

packages/core/src/services/chatCompressionService.ts

@@ -266,7 +266,11 @@ export class ChatCompressionService {
       const threshold =
         (await config.getCompressionThreshold()) ??
         DEFAULT_COMPRESSION_TOKEN_THRESHOLD;
-      if (originalTokenCount < threshold * tokenLimit(model)) {
+      const calculatedLimit = threshold * tokenLimit(model);
+      debugLogger.log(
+        `Checking compression limit: ${originalTokenCount} / ${calculatedLimit} (Threshold: ${threshold})`,
+      );
+      if (originalTokenCount < calculatedLimit) {
         return {
           newHistory: null,
           info: {
@@ -286,14 +290,22 @@ export class ChatCompressionService {
     );
 
     // If summarization previously failed (and not forced), we only rely on truncation.
-    // We do NOT attempt to invoke the LLM for summarization again to avoid repeated failures/costs.
-    if (hasFailedCompressionAttempt && !force) {
+    // We do NOT attempt to invoke the LLM for summarization again to avoid repeated failures/costs,
+    // unless the 'forceCompressionRetries' config flag is set.
+    if (
+      hasFailedCompressionAttempt &&
+      !force &&
+      !config.getForceCompressionRetries()
+    ) {
       const truncatedTokenCount = estimateTokenCountSync(
         truncatedHistory.flatMap((c) => c.parts || []),
       );
 
       // If truncation reduced the size, we consider it a successful "compression" (truncation only).
       if (truncatedTokenCount < originalTokenCount) {
+        debugLogger.log(
+          `Compression previously failed but truncation succeeded. Reduced ${originalTokenCount} to ${truncatedTokenCount} tokens.`,
+        );
         return {
           newHistory: truncatedHistory,
           info: {
@@ -302,16 +314,19 @@ export class ChatCompressionService {
             compressionStatus: CompressionStatus.CONTENT_TRUNCATED,
           },
         };
+      } else {
+        debugLogger.log(
+          'Compression previously failed and truncation did not reduce size. Bypassing summarization.',
+        );
+        return {
+          newHistory: null,
+          info: {
+            originalTokenCount,
+            newTokenCount: originalTokenCount,
+            compressionStatus: CompressionStatus.NOOP,
+          },
+        };
       }
-
-      return {
-        newHistory: null,
-        info: {
-          originalTokenCount,
-          newTokenCount: originalTokenCount,
-          compressionStatus: CompressionStatus.NOOP,
-        },
-      };
     }
 
     const splitPoint = findCompressSplitPoint(