diff --git a/packages/cli/src/ui/commands/chatCommand.test.ts b/packages/cli/src/ui/commands/chatCommand.test.ts
index 0fe485cadd..c934c29dfd 100644
--- a/packages/cli/src/ui/commands/chatCommand.test.ts
+++ b/packages/cli/src/ui/commands/chatCommand.test.ts
@@ -163,7 +163,6 @@ describe('chatCommand', () => {
 
       mockGetHistory.mockReturnValue([
         { role: 'user', parts: [{ text: 'context for our chat' }] },
-        { role: 'model', parts: [{ text: 'Got it. Thanks for the context!' }] },
       ]);
       result = await saveCommand?.action?.(mockContext, tag);
       expect(result).toEqual({
@@ -208,9 +207,7 @@ describe('chatCommand', () => {
     it('should save the conversation if overwrite is confirmed', async () => {
       const history: Content[] = [
         { role: 'user', parts: [{ text: 'context for our chat' }] },
-        { role: 'model', parts: [{ text: 'Got it. Thanks for the context!' }] },
         { role: 'user', parts: [{ text: 'hello' }] },
-        { role: 'model', parts: [{ text: 'Hi there!' }] },
       ];
       mockGetHistory.mockReturnValue(history);
       mockContext.overwriteConfirmed = true;
@@ -263,6 +260,7 @@ describe('chatCommand', () => {
 
     it('should resume a conversation with matching authType', async () => {
       const conversation: Content[] = [
+        { role: 'user', parts: [{ text: 'system setup' }] },
         { role: 'user', parts: [{ text: 'hello gemini' }] },
         { role: 'model', parts: [{ text: 'hello world' }] },
       ];
@@ -285,6 +283,7 @@ describe('chatCommand', () => {
 
     it('should block resuming a conversation with mismatched authType', async () => {
       const conversation: Content[] = [
+        { role: 'user', parts: [{ text: 'system setup' }] },
         { role: 'user', parts: [{ text: 'hello gemini' }] },
         { role: 'model', parts: [{ text: 'hello world' }] },
       ];
@@ -304,6 +303,7 @@ describe('chatCommand', () => {
 
     it('should resume a legacy conversation without authType', async () => {
       const conversation: Content[] = [
+        { role: 'user', parts: [{ text: 'system setup' }] },
         { role: 'user', parts: [{ text: 'hello gemini' }] },
         { role: 'model', parts: [{ text: 'hello world' }] },
       ];
@@ -521,7 +521,6 @@ Hi there!`;
     it('should inform if there is no conversation to share', async () => {
       mockGetHistory.mockReturnValue([
         { role: 'user', parts: [{ text: 'context' }] },
-        { role: 'model', parts: [{ text: 'context response' }] },
       ]);
       const result = await shareCommand?.action?.(mockContext, 'my-chat.json');
       expect(mockFs.writeFile).not.toHaveBeenCalled();
diff --git a/packages/cli/src/ui/commands/chatCommand.ts b/packages/cli/src/ui/commands/chatCommand.ts
index 82390be527..4b0078309c 100644
--- a/packages/cli/src/ui/commands/chatCommand.ts
+++ b/packages/cli/src/ui/commands/chatCommand.ts
@@ -17,6 +17,7 @@ import { CommandKind } from './types.js';
 import {
   decodeTagName,
   type MessageActionReturn,
+  INITIAL_HISTORY_LENGTH,
 } from '@google/gemini-cli-core';
 import path from 'node:path';
 import type {
@@ -131,7 +132,7 @@ const saveCommand: SlashCommand = {
     }
 
     const history = chat.getHistory();
-    if (history.length > 2) {
+    if (history.length > INITIAL_HISTORY_LENGTH) {
       const authType = config?.getContentGeneratorConfig()?.authType;
       await logger.saveCheckpoint({ history, authType }, tag);
       return {
@@ -200,11 +201,8 @@ const resumeCommand: SlashCommand = {
     };
 
     const uiHistory: HistoryItemWithoutId[] = [];
-    let hasSystemPrompt = false;
-    let i = 0;
 
-    for (const item of conversation) {
-      i += 1;
+    for (const item of conversation.slice(INITIAL_HISTORY_LENGTH)) {
       const text =
         item.parts
           ?.filter((m) => !!m.text)
@@ -213,15 +211,11 @@ const resumeCommand: SlashCommand = {
       if (!text) {
         continue;
       }
-      if (i === 1 && text.match(/context for our chat/)) {
-        hasSystemPrompt = true;
-      }
-      if (i > 2 || !hasSystemPrompt) {
-        uiHistory.push({
-          type: (item.role && rolemap[item.role]) || MessageType.GEMINI,
-          text,
-        } as HistoryItemWithoutId);
-      }
+
+      uiHistory.push({
+        type: (item.role && rolemap[item.role]) || MessageType.GEMINI,
+        text,
+      } as HistoryItemWithoutId);
     }
     return {
       type: 'load_history',
@@ -343,10 +337,10 @@ const shareCommand: SlashCommand = {
 
     const history = chat.getHistory();
 
-    // An empty conversation has two hidden messages that setup the context for
+    // An empty conversation has a hidden message that sets up the context for
     // the chat. Thus, to check whether a conversation has been started, we
     // can't check for length 0.
-    if (history.length <= 2) {
+    if (history.length <= INITIAL_HISTORY_LENGTH) {
       return {
         type: 'message',
         messageType: 'info',
diff --git a/packages/core/src/index.ts b/packages/core/src/index.ts
index c73b5d7b95..35804532d8 100644
--- a/packages/core/src/index.ts
+++ b/packages/core/src/index.ts
@@ -73,6 +73,7 @@ export * from './utils/generateContentResponseUtilities.js';
 export * from './utils/filesearch/fileSearch.js';
 export * from './utils/errorParsing.js';
 export * from './utils/workspaceContext.js';
+export * from './utils/environmentContext.js';
 export * from './utils/ignorePatterns.js';
 export * from './utils/partUtils.js';
 export * from './utils/promptIdContext.js';
diff --git a/packages/core/src/utils/environmentContext.ts b/packages/core/src/utils/environmentContext.ts
index 162c2e5961..cad628ce43 100644
--- a/packages/core/src/utils/environmentContext.ts
+++ b/packages/core/src/utils/environmentContext.ts
@@ -8,6 +8,8 @@ import type { Part, Content } from '@google/genai';
 import type { Config } from '../config/config.js';
 import { getFolderStructure } from './getFolderStructure.js';
 
+export const INITIAL_HISTORY_LENGTH = 1;
+
 /**
  * Generates a string describing the current workspace directories and their structures.
  * @param {Config} config - The runtime configuration and services.