diff --git a/integration-tests/file-system.test.ts b/integration-tests/file-system.test.ts
index 64481068c2..522f4e4606 100644
--- a/integration-tests/file-system.test.ts
+++ b/integration-tests/file-system.test.ts
@@ -133,7 +133,7 @@ describe('file-system', () => {
     ).toBeTruthy();
 
     const newFileContent = rig.readFile(fileName);
-    expect(newFileContent).toBe('hello');
+    expect(newFileContent.trim()).toBe('hello');
   });
 
   it('should perform a read-then-write sequence', async () => {
diff --git a/packages/core/src/core/geminiChat.ts b/packages/core/src/core/geminiChat.ts
index b96baa1c6a..1829035d33 100644
--- a/packages/core/src/core/geminiChat.ts
+++ b/packages/core/src/core/geminiChat.ts
@@ -167,8 +167,16 @@ function extractCuratedHistory(comprehensiveHistory: Content[]): Content[] {
   let i = 0;
   while (i < length) {
     if (comprehensiveHistory[i].role === 'user') {
-      curatedHistory.push(comprehensiveHistory[i]);
+      const userMessage: Content = {
+        role: 'user',
+        parts: [...(comprehensiveHistory[i].parts || [])],
+      };
       i++;
+      while (i < length && comprehensiveHistory[i].role === 'user') {
+        userMessage.parts!.push(...(comprehensiveHistory[i].parts || []));
+        i++;
+      }
+      curatedHistory.push(userMessage);
     } else {
       const modelOutput: Content[] = [];
       let isValid = true;
@@ -186,11 +194,6 @@ function extractCuratedHistory(comprehensiveHistory: Content[]): Content[] {
   }
   return curatedHistory;
 }
-
-/**
- * Custom error to signal that a stream completed with invalid content,
- * which should trigger a retry.
- */
 export class InvalidStreamError extends Error {
   readonly type:
     | 'NO_FINISH_REASON'
@@ -342,7 +345,17 @@ export class GeminiChat {
     }
 
     // Add user content to history ONCE before any attempts.
-    this.history.push(userContent);
+    if (
+      this.history.length > 0 &&
+      this.history[this.history.length - 1].role === 'user'
+    ) {
+      const lastUser = this.history[this.history.length - 1];
+      const lastUserParts = lastUser.parts || [];
+      const currentUserParts = userContent.parts || [];
+      lastUser.parts = [...lastUserParts, ...currentUserParts];
+    } else {
+      this.history.push(userContent);
+    }
     const requestContents = this.getHistory(true);
 
     const streamWithRetries = async function* (
diff --git a/packages/core/src/core/turn.ts b/packages/core/src/core/turn.ts
index 9c0e536c48..23dc5f21ec 100644
--- a/packages/core/src/core/turn.ts
+++ b/packages/core/src/core/turn.ts
@@ -5,7 +5,6 @@
  */
 
 import {
-  createUserContent,
   type PartListUnion,
   type GenerateContentResponse,
   type FunctionCall,
@@ -375,10 +374,7 @@ export class Turn {
         throw error;
       }
 
-      const contextForReport = [
-        ...this.chat.getHistory(/*curated*/ true),
-        createUserContent(req),
-      ];
+      const contextForReport = [...this.chat.getHistory(/*curated*/ true)];
       await reportError(
         error,
         'Error when talking to Gemini API',