diff --git a/packages/core/src/context/contextManager.async.test.ts b/packages/core/src/context/contextManager.async.test.ts
index b83f6d751c..2f31b7c19a 100644
--- a/packages/core/src/context/contextManager.async.test.ts
+++ b/packages/core/src/context/contextManager.async.test.ts
@@ -1,4 +1,4 @@
-import { IrMapper } from './ir/mapper.js';
+
 /**
  * @license
  * Copyright 2026 Google LLC
@@ -17,7 +17,7 @@ describe('ContextManager Barrier Tests', () => {
     const { chatHistory, contextManager } = setupContextComponentTest(config);
 
     // 1. Shrink limits: 1 char = 1 token. RetainedTokens = 10. MaxTokens = 100.
-    IrMapper.setConfig({ charsPerToken: 1 });
+    
 
     contextManager['sidecar'].budget.retainedTokens = 5;
     contextManager['sidecar'].budget.maxTokens = 100;
@@ -80,7 +80,6 @@ describe('ContextManager Barrier Tests', () => {
     // 5. Verify Projection shrinks: 6 original messages replaced by 1 snapshot episode (1 text part) -> length 5.
     const projection = await contextManager.projectCompressedHistory();
     expect(projection.length).toBe(5);
-    // console.dir(projection, {depth: null});
     // projection[0] should be the snapshot yield
     expect(projection[0].parts![0].text).toBe('<SNAP>');
   });
@@ -90,7 +89,7 @@ describe('ContextManager Barrier Tests', () => {
     const { chatHistory, contextManager } = setupContextComponentTest(config);
 
     // 1. Shrink limits: maxTokens = 15.
-    IrMapper.setConfig({ charsPerToken: 1 });
+    
     contextManager['sidecar'].budget.maxTokens = 15;
 
     // 2. Build history: 2 turns. Total = 24 tokens.
diff --git a/packages/core/src/context/contextManager.barrier.test.ts b/packages/core/src/context/contextManager.barrier.test.ts
index ce1a6c7fb5..5d8579fe1d 100644
--- a/packages/core/src/context/contextManager.barrier.test.ts
+++ b/packages/core/src/context/contextManager.barrier.test.ts
@@ -5,7 +5,7 @@
  */
 
 import { describe, it, expect, vi, beforeEach, afterEach } from 'vitest';
-import { IrMapper } from './ir/mapper.js';
+
 import {
   createSyntheticHistory,
   createMockContextConfig,
@@ -46,7 +46,7 @@ describe('ContextManager Sync Pressure Barrier Tests', () => {
     ]);
 
     const rawHistoryLength = chatHistory.get().length;
-    IrMapper.setConfig({ charsPerToken: 1 });
+    
 
     // 5. Project History (Triggers Sync Barrier)
     const projection = await contextManager.projectCompressedHistory();
diff --git a/packages/core/src/context/contextManager.golden.test.ts b/packages/core/src/context/contextManager.golden.test.ts
index 9eb05ff620..d5a2f6950c 100644
--- a/packages/core/src/context/contextManager.golden.test.ts
+++ b/packages/core/src/context/contextManager.golden.test.ts
@@ -18,6 +18,7 @@ import { ContextEnvironmentImpl } from './sidecar/environmentImpl.js';
 import { SidecarLoader } from './sidecar/SidecarLoader.js';
 import { ContextTracer } from './tracer.js';
 import { ContextEventBus } from './eventBus.js';
+import { ContextTokenCalculator } from './utils/contextTokenCalculator.js';
 
 import type { Content } from '@google/genai';
 
@@ -46,6 +47,7 @@ describe('ContextManager Golden Tests', () => {
   beforeEach(() => {
     mockConfig = {
       isContextManagementEnabled: vi.fn().mockReturnValue(true),
+      getExperimentalContextSidecarConfig: vi.fn().mockReturnValue(undefined),
       getTargetDir: vi.fn().mockReturnValue('/tmp'),
       getSessionId: vi.fn().mockReturnValue('test-session'),
       getToolOutputMaskingConfig: vi.fn().mockResolvedValue({
@@ -68,7 +70,7 @@ describe('ContextManager Golden Tests', () => {
       }),
     };
 
-    const sidecar = SidecarLoader.fromLegacyConfig(mockConfig as any);
+    const sidecar = SidecarLoader.fromConfig(mockConfig as any);
     const tracer = new ContextTracer('/tmp', 'test-session');
     const eventBus = new ContextEventBus();
     const env = new ContextEnvironmentImpl(
@@ -118,7 +120,7 @@ describe('ContextManager Golden Tests', () => {
     const history = createLargeHistory();
     (contextManager as any).pristineEpisodes = (
       await import('./ir/mapper.js')
-    ).IrMapper.toIr(history);
+    ).IrMapper.toIr(history, new ContextTokenCalculator(4));
     const result = await contextManager.projectCompressedHistory();
     expect(result).toMatchSnapshot();
   });
@@ -127,7 +129,7 @@ describe('ContextManager Golden Tests', () => {
     const history = createLargeHistory();
     (contextManager as any).pristineEpisodes = (
       await import('./ir/mapper.js')
-    ).IrMapper.toIr(history);
+    ).IrMapper.toIr(history, new ContextTokenCalculator(4));
     // In Golden Tests, we just want to ensure the logic doesn't throw or alter unprotected history in weird ways.
     // Since we're skipping processors due to being under budget, it should equal history.
     const tracer2 = new ContextTracer('/tmp', 'test2');
@@ -153,7 +155,7 @@ describe('ContextManager Golden Tests', () => {
 
     (contextManager as any).pristineEpisodes = (
       await import('./ir/mapper.js')
-    ).IrMapper.toIr(history);
+    ).IrMapper.toIr(history, new ContextTokenCalculator(4));
     const result = await contextManager.projectCompressedHistory();
 
     expect(result.length).toEqual(history.length);
diff --git a/packages/core/src/context/contextManager.ts b/packages/core/src/context/contextManager.ts
index f5f23abccb..f70f66b562 100644
--- a/packages/core/src/context/contextManager.ts
+++ b/packages/core/src/context/contextManager.ts
@@ -21,7 +21,7 @@ import type { SidecarConfig } from './sidecar/types.js';
 import { ProcessorRegistry } from './sidecar/registry.js';
 import { PipelineOrchestrator } from './sidecar/orchestrator.js';
 import { HistoryObserver } from './historyObserver.js';
-import { calculateEpisodeListTokens } from './utils/contextTokenCalculator.js';
+
 import { generateWorkingBufferView } from './ir/graphUtils.js';
 
 
@@ -63,6 +63,11 @@ export class ContextManager {
 
     this.orchestrator = new PipelineOrchestrator(this.sidecar, this.env, this.eventBus, this.tracer);
 
+    this.eventBus.onPristineHistoryUpdated((event) => {
+      this.pristineEpisodes = event.episodes;
+      this.evaluateTriggers();
+    });
+
     this.eventBus.onVariantReady((event) => {
       
       // Find the target episode in the pristine graph
@@ -92,6 +97,32 @@ export class ContextManager {
     }
   }
 
+  /**
+   * Evaluates if the current working buffer exceeds configured budget thresholds,
+   * firing consolidation events if necessary.
+   */
+  private evaluateTriggers() {
+    if (!this.sidecar.budget) return;
+
+    const workingBuffer = this.getWorkingBufferView();
+    const currentTokens = this.env.tokenCalculator.calculateEpisodeListTokens(workingBuffer);
+    
+    this.tracer.logEvent('ContextManager', 'Evaluated triggers', { currentTokens, retainedTokens: this.sidecar.budget.retainedTokens });
+
+    // 1. Eager Compute Trigger
+    this.eventBus.emitChunkReceived({ episodes: this.pristineEpisodes });
+
+    // 2. Budget Crossed Trigger
+    if (currentTokens > this.sidecar.budget.retainedTokens) {
+      const deficit = currentTokens - this.sidecar.budget.retainedTokens;
+      this.tracer.logEvent('ContextManager', 'Budget crossed. Emitting ConsolidationNeeded', { deficit });
+      this.eventBus.emitConsolidationNeeded({
+        episodes: workingBuffer, 
+        targetDeficit: deficit,
+      });
+    }
+  }
+
   /**
    * Subscribes to the core AgentChatHistory to natively track all message events,
    * converting them seamlessly into pristine Episodes.
@@ -105,10 +136,7 @@ export class ContextManager {
       chatHistory,
       this.eventBus,
       this.tracer,
-      this.sidecar,
-      (episodes) => { this.pristineEpisodes = episodes; },
-      () => this.getWorkingBufferView(),
-      (episodes) => calculateEpisodeListTokens(episodes)
+      this.env.tokenCalculator,
     );
 
     this.historyObserver.start();
@@ -125,7 +153,8 @@ export class ContextManager {
     return generateWorkingBufferView(
       this.pristineEpisodes,
       this.sidecar.budget.retainedTokens,
-      this.tracer
+      this.tracer,
+      this.env
     );
   }
 
diff --git a/packages/core/src/context/eventBus.ts b/packages/core/src/context/eventBus.ts
index dc9e8b5b74..2fed823c4c 100644
--- a/packages/core/src/context/eventBus.ts
+++ b/packages/core/src/context/eventBus.ts
@@ -7,6 +7,10 @@
 import { EventEmitter } from 'node:events';
 import type { Episode, Variant } from './ir/types.js';
 
+export interface PristineHistoryUpdatedEvent {
+  episodes: Episode[];
+}
+
 export interface ContextConsolidationEvent {
   episodes: Episode[];
   targetDeficit: number;
@@ -23,6 +27,14 @@ export interface VariantReadyEvent {
 }
 
 export class ContextEventBus extends EventEmitter {
+  emitPristineHistoryUpdated(event: PristineHistoryUpdatedEvent) {
+    this.emit('PRISTINE_HISTORY_UPDATED', event);
+  }
+
+  onPristineHistoryUpdated(listener: (event: PristineHistoryUpdatedEvent) => void) {
+    this.on('PRISTINE_HISTORY_UPDATED', listener);
+  }
+
   emitChunkReceived(event: IrChunkReceivedEvent) {
     this.emit('IR_CHUNK_RECEIVED', event);
   }
diff --git a/packages/core/src/context/historyObserver.ts b/packages/core/src/context/historyObserver.ts
index f46e9f5a0f..e6132d3873 100644
--- a/packages/core/src/context/historyObserver.ts
+++ b/packages/core/src/context/historyObserver.ts
@@ -6,10 +6,9 @@
 
 import type { AgentChatHistory, HistoryEvent } from '../core/agentChatHistory.js';
 import { IrMapper } from './ir/mapper.js';
+import type { ContextTokenCalculator } from './utils/contextTokenCalculator.js';
 import type { ContextEventBus } from './eventBus.js';
 import type { ContextTracer } from './tracer.js';
-import type { SidecarConfig } from './sidecar/types.js';
-import type { Episode } from './ir/types.js';
 
 /**
  * Connects the raw AgentChatHistory to the ContextManager.
@@ -23,10 +22,7 @@ export class HistoryObserver {
     private readonly chatHistory: AgentChatHistory,
     private readonly eventBus: ContextEventBus,
     private readonly tracer: ContextTracer,
-    private readonly sidecar: SidecarConfig,
-    private readonly onIrRebuilt: (episodes: Episode[]) => void,
-    private readonly computeWorkingBuffer: () => Episode[],
-    private readonly calculateIrTokens: (episodes: Episode[]) => number,
+    private readonly tokenCalculator: ContextTokenCalculator,
   ) {}
 
   start() {
@@ -36,11 +32,10 @@ export class HistoryObserver {
 
     this.unsubscribeHistory = this.chatHistory.subscribe((_event: HistoryEvent) => {
       // Rebuild the pristine IR graph from the full source history on every change.
-      const pristineEpisodes = IrMapper.toIr(this.chatHistory.get(), this.sidecar.tokenCalculator);
+      const pristineEpisodes = IrMapper.toIr(this.chatHistory.get(), this.tokenCalculator);
       this.tracer.logEvent('HistoryObserver', 'Rebuilt pristine graph from chat history update', { episodeCount: pristineEpisodes.length });
       
-      this.onIrRebuilt(pristineEpisodes);
-      this.checkTriggers(pristineEpisodes);
+      this.eventBus.emitPristineHistoryUpdated({ episodes: pristineEpisodes });
     });
   }
 
@@ -50,26 +45,4 @@ export class HistoryObserver {
       this.unsubscribeHistory = undefined;
     }
   }
-
-  private checkTriggers(pristineEpisodes: Episode[]) {
-    if (!this.sidecar.budget) return;
-
-    const workingBuffer = this.computeWorkingBuffer();
-    const currentTokens = this.calculateIrTokens(workingBuffer);
-    
-    this.tracer.logEvent('HistoryObserver', 'Evaluated triggers', { currentTokens, retainedTokens: this.sidecar.budget.retainedTokens });
-
-    // 1. Eager Compute Trigger
-    this.eventBus.emitChunkReceived({ episodes: pristineEpisodes });
-
-    // 2. Budget Crossed Trigger
-    if (currentTokens > this.sidecar.budget.retainedTokens) {
-      const deficit = currentTokens - this.sidecar.budget.retainedTokens;
-      this.tracer.logEvent('HistoryObserver', 'Budget crossed. Emitting ConsolidationNeeded', { deficit });
-      this.eventBus.emitConsolidationNeeded({
-        episodes: workingBuffer, 
-        targetDeficit: deficit,
-      });
-    }
-  }
 }
diff --git a/packages/core/src/context/ir/graphUtils.ts b/packages/core/src/context/ir/graphUtils.ts
index 1f3edf707f..4bc801ad71 100644
--- a/packages/core/src/context/ir/graphUtils.ts
+++ b/packages/core/src/context/ir/graphUtils.ts
@@ -7,7 +7,7 @@
 import type { Episode } from './types.js';
 import type { ContextTracer } from '../tracer.js';
 import { debugLogger } from '../../utils/debugLogger.js';
-import { calculateEpisodeListTokens } from '../utils/contextTokenCalculator.js';
+
 
 /**
  * Generates a computed view of the pristine log.
@@ -16,10 +16,13 @@ import { calculateEpisodeListTokens } from '../utils/contextTokenCalculator.js';
  * (snapshot > summary > masked) instead of the raw text.
  * Handles N-to-1 variant skipping automatically.
  */
+import type { ContextEnvironment } from "../sidecar/environment.js";
+
 export function generateWorkingBufferView(
   pristineEpisodes: Episode[],
   retainedTokens: number,
   tracer: ContextTracer,
+  env: ContextEnvironment,
 ): Episode[] {
   let currentEpisodes: Episode[] = [];
   let rollingTokens = 0;
@@ -72,7 +75,7 @@ export function generateWorkingBufferView(
         : undefined,
     };
 
-    const epTokens = calculateEpisodeListTokens([projectedEp]);
+    const epTokens = env.tokenCalculator.calculateEpisodeListTokens([projectedEp]);
 
     if (rollingTokens > retainedTokens && ep.variants) {
       const snapshot = ep.variants['snapshot'];
@@ -153,7 +156,7 @@ export function generateWorkingBufferView(
     }
 
     currentEpisodes.unshift(projectedEp);
-    rollingTokens += calculateEpisodeListTokens([projectedEp]);
+    rollingTokens += env.tokenCalculator.calculateEpisodeListTokens([projectedEp]);
   }
 
   return currentEpisodes;
diff --git a/packages/core/src/context/ir/mapper.test.ts b/packages/core/src/context/ir/mapper.test.ts
index 27b401dcd8..bb2365661c 100644
--- a/packages/core/src/context/ir/mapper.test.ts
+++ b/packages/core/src/context/ir/mapper.test.ts
@@ -6,6 +6,7 @@
 
 import { describe, it, expect } from 'vitest';
 import { IrMapper } from './mapper.js';
+import { ContextTokenCalculator } from '../utils/contextTokenCalculator.js';
 import type { Content } from '@google/genai';
 import type { UserPrompt, ToolExecution } from './types.js';
 
@@ -80,7 +81,8 @@ describe('IrMapper', () => {
       { role: 'model', parts: [{ text: 'Everything is done!' }] },
     ];
 
-    const episodes = IrMapper.toIr(rawHistory);
+    const tokenCalculator = new ContextTokenCalculator(4);
+    const episodes = IrMapper.toIr(rawHistory, tokenCalculator);
 
     expect(episodes).toHaveLength(1);
     const ep = episodes[0];
@@ -135,7 +137,8 @@ describe('IrMapper', () => {
       { role: 'model', parts: [{ text: 'Hi there' }] },
     ];
 
-    const initialIr = IrMapper.toIr(history);
+    const tokenCalculator = new ContextTokenCalculator(4);
+    const initialIr = IrMapper.toIr(history, tokenCalculator);
     expect(initialIr).toHaveLength(1);
 
     // Save the uniquely generated deterministic ID for the first episode
@@ -146,7 +149,7 @@ describe('IrMapper', () => {
     history.push({ role: 'user', parts: [{ text: 'How are you?' }] });
     history.push({ role: 'model', parts: [{ text: 'I am an AI.' }] });
 
-    const updatedIr = IrMapper.toIr(history);
+    const updatedIr = IrMapper.toIr(history, tokenCalculator);
     expect(updatedIr).toHaveLength(2);
 
     // 3. Verify ID Stability
diff --git a/packages/core/src/context/ir/projector.ts b/packages/core/src/context/ir/projector.ts
index 75aae8d85b..48e80f3ba7 100644
--- a/packages/core/src/context/ir/projector.ts
+++ b/packages/core/src/context/ir/projector.ts
@@ -11,7 +11,7 @@ import { debugLogger } from '../../utils/debugLogger.js';
 import type { ContextEnvironment, ContextTracer } from '../sidecar/environment.js';
 import type { PipelineOrchestrator } from '../sidecar/orchestrator.js';
 import type { SidecarConfig } from '../sidecar/types.js';
-import { calculateEpisodeListTokens } from '../utils/contextTokenCalculator.js';
+
 
 export class IrProjector {
   /**
@@ -31,7 +31,7 @@ export class IrProjector {
     }
 
     const maxTokens = sidecar.budget.maxTokens;
-    let currentTokens = calculateEpisodeListTokens(workingBuffer);
+    let currentTokens = env.tokenCalculator.calculateEpisodeListTokens(workingBuffer);
 
     if (currentTokens <= maxTokens) {
       tracer.logEvent('IrProjector', `View is within maxTokens (${currentTokens} <= ${maxTokens}). Returning view.`);
@@ -50,7 +50,7 @@ export class IrProjector {
       isBudgetSatisfied: currentTokens <= sidecar.budget.maxTokens, 
     });
 
-    const finalTokens = calculateEpisodeListTokens(processedEpisodes);
+    const finalTokens = env.tokenCalculator.calculateEpisodeListTokens(processedEpisodes);
     tracer.logEvent('IrProjector', `Finished projection. Final token count: ${finalTokens}.`);
     debugLogger.log(`Context Manager finished. Final actual token count: ${finalTokens}.`);
 
diff --git a/packages/core/src/context/processors/blobDegradationProcessor.ts b/packages/core/src/context/processors/blobDegradationProcessor.ts
index 2857e5764d..11a8e26b98 100644
--- a/packages/core/src/context/processors/blobDegradationProcessor.ts
+++ b/packages/core/src/context/processors/blobDegradationProcessor.ts
@@ -6,7 +6,7 @@
 import type { Episode } from '../ir/types.js';
 import type { ContextAccountingState, ContextProcessor } from '../pipeline.js';
 import type { ContextEnvironment } from '../sidecar/environment.js';
-import { estimateContextTokenCountSync as estimateTokenCountSync } from '../utils/contextTokenCalculator.js';
+
 import { sanitizeFilenamePart } from '../../utils/fileUtils.js';
 import * as fsPromises from 'node:fs/promises';
 import path from 'node:path';
@@ -80,30 +80,28 @@ export class BlobDegradationProcessor implements ContextProcessor {
             newText = `[Multi-Modal Blob (${part.mimeType}, ${mb}MB) degraded to text to preserve context window. Saved to: ${filePath}]`;
 
             // Re-calculate tokens. Images are expensive (~258 tokens). The text is cheap (~20 tokens).
-            const oldTokens = estimateTokenCountSync([
+            const oldTokens = this.env.tokenCalculator.estimateTokensForParts([
               { inlineData: { mimeType: part.mimeType, data: part.data } },
             ]);
-            const newTokens = estimateTokenCountSync([{ text: newText }]);
+            const newTokens = this.env.tokenCalculator.estimateTokensForParts([{ text: newText }]);
             tokensSaved = oldTokens - newTokens;
           } else if (part.type === 'file_data') {
             newText = `[File Reference (${part.mimeType}) degraded to text to preserve context window. Original URI: ${part.fileUri}]`;
-            const oldTokens = estimateTokenCountSync([
+            const oldTokens = this.env.tokenCalculator.estimateTokensForParts([
               { fileData: { mimeType: part.mimeType, fileUri: part.fileUri } },
             ]);
-            const newTokens = estimateTokenCountSync([{ text: newText }]);
+            const newTokens = this.env.tokenCalculator.estimateTokensForParts([{ text: newText }]);
             tokensSaved = oldTokens - newTokens;
           } else if (part.type === 'raw_part') {
             newText = `[Unknown Part degraded to text to preserve context window.]`;
             // eslint-disable-next-line @typescript-eslint/no-unsafe-type-assertion
-            const oldTokens = estimateTokenCountSync([part.part as Part]);
-            const newTokens = estimateTokenCountSync([{ text: newText }]);
+            const oldTokens = this.env.tokenCalculator.estimateTokensForParts([part.part as Part]);
+            const newTokens = this.env.tokenCalculator.estimateTokensForParts([{ text: newText }]);
             tokensSaved = oldTokens - newTokens;
           }
 
           if (newText && tokensSaved > 0) {
-            const newTokens = estimateTokenCountSync([{ text: newText }], 0, {
-              charsPerToken: this.env.charsPerToken,
-            });
+            const newTokens = this.env.tokenCalculator.estimateTokensForParts([{ text: newText }]);
             part.presentation = { text: newText, tokens: newTokens };
 
             ep.trigger.metadata.transformations.push({
diff --git a/packages/core/src/context/processors/emergencyTruncationProcessor.ts b/packages/core/src/context/processors/emergencyTruncationProcessor.ts
index 3611933555..6d2b8c0278 100644
--- a/packages/core/src/context/processors/emergencyTruncationProcessor.ts
+++ b/packages/core/src/context/processors/emergencyTruncationProcessor.ts
@@ -7,7 +7,7 @@
 import type { ContextProcessor, ContextAccountingState } from '../pipeline.js';
 import type { Episode } from '../ir/types.js';
 import type { ContextEnvironment } from '../sidecar/environment.js';
-import { calculateEpisodeListTokens } from '../utils/contextTokenCalculator.js';
+
 
 export interface EmergencyTruncationProcessorOptions {}
 
@@ -19,7 +19,7 @@ export class EmergencyTruncationProcessor implements ContextProcessor {
   readonly id = 'EmergencyTruncationProcessor';
   readonly name = 'EmergencyTruncationProcessor';
   readonly options: EmergencyTruncationProcessorOptions;
-  constructor(_env: ContextEnvironment, options: EmergencyTruncationProcessorOptions) {
+  constructor(private readonly _env: ContextEnvironment, options: EmergencyTruncationProcessorOptions) {
     this.options = options;
   }
 
@@ -32,7 +32,7 @@ export class EmergencyTruncationProcessor implements ContextProcessor {
     
     // We respect the global protected Episode IDs (like the system prompt at index 0)
     for (const ep of episodes) {
-      const epTokens = calculateEpisodeListTokens([ep]);
+      const epTokens = this._env.tokenCalculator.calculateEpisodeListTokens([ep]);
       
       if (remainingTokens > targetTokens && !state.protectedEpisodeIds.has(ep.id)) {
         remainingTokens -= epTokens;
diff --git a/packages/core/src/context/processors/semanticCompressionProcessor.ts b/packages/core/src/context/processors/semanticCompressionProcessor.ts
index d38fe1d1f0..f82f2c6652 100644
--- a/packages/core/src/context/processors/semanticCompressionProcessor.ts
+++ b/packages/core/src/context/processors/semanticCompressionProcessor.ts
@@ -10,7 +10,7 @@ import type { ContextEnvironment } from '../sidecar/environment.js';
 import { debugLogger } from '../../utils/debugLogger.js';
 import { LlmRole } from '../../telemetry/types.js';
 import { getResponseText } from '../../utils/partUtils.js';
-import { estimateContextTokenCountSync } from '../utils/contextTokenCalculator.js';
+
 
 export class SemanticCompressionProcessor implements ContextProcessor {
   readonly name = 'SemanticCompression';
@@ -62,8 +62,8 @@ export class SemanticCompressionProcessor implements ContextProcessor {
               part.text,
               'User Prompt',
             );
-            const newTokens = estimateContextTokenCountSync([{ text: summary }], 0, { charsPerToken: this.env.charsPerToken });
-            const oldTokens = estimateContextTokenCountSync([{ text: part.text }], 0, { charsPerToken: this.env.charsPerToken });
+            const newTokens = this.env.tokenCalculator.estimateTokensForParts([{ text: summary }]);
+            const oldTokens = this.env.tokenCalculator.estimateTokensForParts([{ text: part.text }]);
 
             if (newTokens < oldTokens) {
               part.presentation = { text: summary, tokens: newTokens };
@@ -88,8 +88,8 @@ export class SemanticCompressionProcessor implements ContextProcessor {
               step.text,
               'Agent Thought',
             );
-            const newTokens = estimateContextTokenCountSync([{ text: summary }], 0, { charsPerToken: this.env.charsPerToken });
-            const oldTokens = estimateContextTokenCountSync([{ text: step.text }], 0, { charsPerToken: this.env.charsPerToken });
+            const newTokens = this.env.tokenCalculator.estimateTokensForParts([{ text: summary }]);
+            const oldTokens = this.env.tokenCalculator.estimateTokensForParts([{ text: step.text }]);
 
             if (newTokens < oldTokens) {
               step.presentation = { text: summary, tokens: newTokens };
@@ -130,7 +130,7 @@ export class SemanticCompressionProcessor implements ContextProcessor {
             // Wrap the summary in an object so the Gemini API accepts it as a valid functionResponse.response
             const newObsObject = { summary };
 
-            const newObsTokens = estimateContextTokenCountSync([
+            const newObsTokens = this.env.tokenCalculator.estimateTokensForParts([
               {
                 functionResponse: {
                   name: step.toolName,
@@ -138,7 +138,7 @@ export class SemanticCompressionProcessor implements ContextProcessor {
                   id: step.id,
                 },
               },
-            ], 0, { charsPerToken: this.env.charsPerToken });
+            ]);
 
             const oldObsTokens =
               step.presentation?.tokens.observation ?? step.tokens.observation;
diff --git a/packages/core/src/context/processors/stateSnapshotProcessor.ts b/packages/core/src/context/processors/stateSnapshotProcessor.ts
index b158b1c80d..4761cb9eb2 100644
--- a/packages/core/src/context/processors/stateSnapshotProcessor.ts
+++ b/packages/core/src/context/processors/stateSnapshotProcessor.ts
@@ -7,9 +7,10 @@
 import type { ContextProcessor, ContextAccountingState } from '../pipeline.js';
 import type { Episode, ToolExecution } from '../ir/types.js';
 import type { ContextEnvironment, ContextEventBus } from '../sidecar/environment.js';
-import { estimateContextTokenCountSync as estimateTokenCountSync } from '../utils/contextTokenCalculator.js';
+
 import { v4 as uuidv4 } from 'uuid';
 import { LlmRole } from '../../telemetry/llmRole.js';
+import { debugLogger } from 'src/utils/debugLogger.js';
 
 export interface StateSnapshotProcessorOptions {
   model?: string;
@@ -48,7 +49,7 @@ export class StateSnapshotProcessor implements ContextProcessor {
       for (let i = 1; i < episodes.length - 1; i++) {
         const ep = episodes[i];
         selectedEpisodes.push(ep);
-        deficitAccumulator += estimateTokenCountSync([
+        deficitAccumulator += this.env.tokenCalculator.estimateTokensForParts([
           { text: (ep.trigger as any)?.semanticParts?.[0]?.text ?? '' },
           { text: ep.yield?.text ?? '' },
         ]);
@@ -116,7 +117,7 @@ Output ONLY the raw factual snapshot, formatted compactly. Do not include markdo
 
       // Synthesize a new "Episode" representing this compressed block
       const newId = uuidv4();
-      const contentTokens = estimateTokenCountSync([{ text: snapshotText }]);
+      const contentTokens = this.env.tokenCalculator.estimateTokensForParts([{ text: snapshotText }]);
 
       return {
         id: newId,
@@ -144,7 +145,7 @@ Output ONLY the raw factual snapshot, formatted compactly. Do not include markdo
         },
       };
     } catch (error) {
-      console.error('Failed to synthesize snapshot:', error);
+      debugLogger.error('Failed to synthesize snapshot:', error);
       throw error;
     }
   }
diff --git a/packages/core/src/context/processors/toolMaskingProcessor.ts b/packages/core/src/context/processors/toolMaskingProcessor.ts
index c50788fb83..cc560392cd 100644
--- a/packages/core/src/context/processors/toolMaskingProcessor.ts
+++ b/packages/core/src/context/processors/toolMaskingProcessor.ts
@@ -6,7 +6,7 @@
 
 import type { ContextAccountingState, ContextProcessor } from '../pipeline.js';
 import type { ContextEnvironment } from '../sidecar/environment.js';
-import { estimateContextTokenCountSync } from '../utils/contextTokenCalculator.js';
+
 import { sanitizeFilenamePart } from '../../utils/fileUtils.js';
 import * as fsPromises from 'node:fs/promises';
 import path from 'node:path';
@@ -173,7 +173,7 @@ export class ToolMaskingProcessor implements ContextProcessor {
           step.presentation.observation = obsRes.masked;
 
           // Recalculate tokens perfectly
-          const newIntentTokens = estimateTokenCountSync([
+          const newIntentTokens = this.env.tokenCalculator.estimateTokensForParts([
             {
               functionCall: {
                 name: toolName,
@@ -182,7 +182,7 @@ export class ToolMaskingProcessor implements ContextProcessor {
               },
             },
           ]);
-          const newObsTokens = estimateTokenCountSync([
+          const newObsTokens = this.env.tokenCalculator.estimateTokensForParts([
             {
               functionResponse: {
                 name: toolName,
diff --git a/packages/core/src/context/sidecar/SidecarLoader.ts b/packages/core/src/context/sidecar/SidecarLoader.ts
index 3040c3d7b2..9079dee792 100644
--- a/packages/core/src/context/sidecar/SidecarLoader.ts
+++ b/packages/core/src/context/sidecar/SidecarLoader.ts
@@ -8,23 +8,20 @@ import * as fs from 'node:fs';
 import type { Config } from '../../config/config.js';
 import type { SidecarConfig } from './types.js';
 import { defaultSidecarProfile } from './profiles.js';
+import { debugLogger } from 'src/utils/debugLogger.js';
 
 export class SidecarLoader {
   /**
    * Generates a Sidecar JSON graph from the experimental config file path or defaults.
    */
   static fromConfig(config: Config): SidecarConfig {
-    const sidecarPath =
-      typeof (config as any).getExperimentalContextSidecarConfig === 'function'
-        ? (config as any).getExperimentalContextSidecarConfig()
-        : undefined;
-
+    const sidecarPath = config.getExperimentalContextSidecarConfig()
     if (sidecarPath && fs.existsSync(sidecarPath)) {
       try {
         const fileContent = fs.readFileSync(sidecarPath, 'utf8');
         return JSON.parse(fileContent) as SidecarConfig;
       } catch (error) {
-        console.error(
+        debugLogger.error(
           `Failed to parse Sidecar configuration file at ${sidecarPath}:`,
           error,
         );
@@ -34,8 +31,4 @@ export class SidecarLoader {
 
     return defaultSidecarProfile;
   }
-
-  static fromLegacyConfig(config: Config): SidecarConfig {
-    return SidecarLoader.fromConfig(config);
-  }
 }
diff --git a/packages/core/src/context/testing/contextTestUtils.ts b/packages/core/src/context/testing/contextTestUtils.ts
index 6a855c783f..4d5b4811a4 100644
--- a/packages/core/src/context/testing/contextTestUtils.ts
+++ b/packages/core/src/context/testing/contextTestUtils.ts
@@ -77,6 +77,7 @@ export function createMockContextConfig(
     getUsageStatisticsEnabled: vi.fn().mockReturnValue(false),
     getTargetDir: vi.fn().mockReturnValue('/tmp'),
     getSessionId: vi.fn().mockReturnValue('test-session'),
+    getExperimentalContextSidecarConfig: vi.fn().mockReturnValue(undefined),
   };
 
   // eslint-disable-next-line @typescript-eslint/no-unsafe-type-assertion
@@ -95,7 +96,7 @@ import type { BaseLlmClient } from 'src/core/baseLlmClient.js';
 
 export function setupContextComponentTest(config: Config) {
   const chatHistory = new AgentChatHistory();
-  const sidecar = SidecarLoader.fromLegacyConfig(config);
+  const sidecar = SidecarLoader.fromConfig(config);
   const tracer = new ContextTracer('/tmp', 'test-session');
   const eventBus = new ContextEventBus();
   const env = new ContextEnvironmentImpl(
diff --git a/packages/core/src/context/tracer.ts b/packages/core/src/context/tracer.ts
index 20baced9fc..00ffa1a9ca 100644
--- a/packages/core/src/context/tracer.ts
+++ b/packages/core/src/context/tracer.ts
@@ -7,6 +7,7 @@
 import * as fs from 'node:fs';
 import * as path from 'node:path';
 import { randomUUID } from 'node:crypto';
+import { debugLogger } from '../utils/debugLogger.js';
 
 export class ContextTracer {
   private traceDir: string;
@@ -23,7 +24,7 @@ export class ContextTracer {
         fs.mkdirSync(this.assetsDir, { recursive: true });
         this.logEvent('SYSTEM', 'Context Tracer Initialized', { sessionId });
       } catch (e) {
-        console.error('Failed to initialize ContextTracer', e);
+        debugLogger.error('Failed to initialize ContextTracer', e);
         this.enabled = false;
       }
     }
diff --git a/packages/core/src/context/utils/contextTokenCalculator.ts b/packages/core/src/context/utils/contextTokenCalculator.ts
index 7590965775..cc73fc5de9 100644
--- a/packages/core/src/context/utils/contextTokenCalculator.ts
+++ b/packages/core/src/context/utils/contextTokenCalculator.ts
@@ -8,6 +8,12 @@ import type { Part } from '@google/genai';
 import { estimateTokenCountSync as baseEstimate } from '../../utils/tokenCalculation.js';
 import type { Episode } from '../ir/types.js';
 
+/**
+ * The flat token cost assigned to a single multi-modal asset (like an image tile)
+ * by the Gemini API. We use this as a baseline heuristic for inlineData/fileData.
+ */
+const BASE_MULTIMODAL_TOKEN_COST = 258;
+
 export class ContextTokenCalculator {
   constructor(private readonly charsPerToken: number) {}
 
@@ -47,21 +53,19 @@ export class ContextTokenCalculator {
    * Deeply inspects the nested structure and uses the base tokenization math.
    */
   estimateTokensForParts(parts: Part[], depth: number = 0): number {
-    if (this.charsPerToken !== 4) {
-      let totalTokens = 0;
-      for (const part of parts) {
-        if (typeof part.text === 'string') {
-          totalTokens += Math.ceil(part.text.length / this.charsPerToken);
-        } else {
-          totalTokens += Math.ceil(
-            JSON.stringify(part).length / this.charsPerToken,
-          );
-        }
+    let totalTokens = 0;
+    for (const part of parts) {
+      if (typeof part.text === 'string') {
+        totalTokens += Math.ceil(part.text.length / this.charsPerToken);
+      } else if (part.inlineData !== undefined || part.fileData !== undefined) {
+        totalTokens += BASE_MULTIMODAL_TOKEN_COST;
+      } else {
+        totalTokens += Math.ceil(
+          JSON.stringify(part).length / this.charsPerToken,
+        );
       }
-      return totalTokens;
     }
-
-    // The baseEstimate no longer accepts config because we forked it!
-    return baseEstimate(parts, depth);
+    // Also include structural overhead
+    return totalTokens + baseEstimate(parts, depth);
   }
 }