diff --git a/package.json b/package.json
index 737bc3d..5b97e09 100644
--- a/package.json
+++ b/package.json
@@ -1,6 +1,6 @@
 {
   "name": "hermes-web-ui",
-  "version": "0.5.23",
+  "version": "0.5.24",
   "description": "Self-hosted AI chat dashboard for Hermes Agent — multi-model web UI with multi-platform integration",
   "repository": {
     "type": "git",
diff --git a/packages/client/src/data/changelog.ts b/packages/client/src/data/changelog.ts
index 4595768..fb48edd 100644
--- a/packages/client/src/data/changelog.ts
+++ b/packages/client/src/data/changelog.ts
@@ -5,6 +5,13 @@ export interface ChangelogEntry {
 }
 
 export const changelog: ChangelogEntry[] = [
+  {
+    version: '0.5.24',
+    date: '2026-05-15',
+    changes: [
+      'changelog.new_0_5_24_1',
+    ],
+  },
   {
     version: '0.5.23',
     date: '2026-05-15',
diff --git a/packages/client/src/i18n/locales/de.ts b/packages/client/src/i18n/locales/de.ts
index 7fab6aa..bc9d597 100644
--- a/packages/client/src/i18n/locales/de.ts
+++ b/packages/client/src/i18n/locales/de.ts
@@ -876,6 +876,7 @@ jobTriggered: 'Job ausgelost',
     new_0_5_23_3: 'Isolate gateway profile environment variables to prevent credentials leaking across profiles',
     new_0_5_23_4: 'Reserve the Web UI port during gateway allocation to avoid startup conflicts',
     new_0_5_23_5: 'Fix self-update restart handling so successful helper exits are not reported as failures',
+    new_0_5_24_1: 'Align Bridge chat with API Server handling for multimodal input, system prompt, and workspace context',
     new_0_5_5_1: '🎉 Tag der Arbeit! Heute wird nicht gearbeitet, bitte habt Verständnis',
     new_0_5_5_2: 'Verlaufsseite für Hermes-Sitzungshistorie hinzugefügt',
     new_0_5_5_3: 'Verlaufsseite verwaltet Sitzungen unabhängig ohne Störung des aktiven Chats',
diff --git a/packages/client/src/i18n/locales/en.ts b/packages/client/src/i18n/locales/en.ts
index 0b06d7e..a6a44c0 100644
--- a/packages/client/src/i18n/locales/en.ts
+++ b/packages/client/src/i18n/locales/en.ts
@@ -1153,6 +1153,7 @@ export default {
     new_0_5_23_3: 'Isolate gateway profile environment variables to prevent credentials leaking across profiles',
     new_0_5_23_4: 'Reserve the Web UI port during gateway allocation to avoid startup conflicts',
     new_0_5_23_5: 'Fix self-update restart handling so successful helper exits are not reported as failures',
+    new_0_5_24_1: 'Align Bridge chat with API Server handling for multimodal input, system prompt, and workspace context',
 
     new_0_5_6_1: 'Add voice playback feature with Web Speech API: manual button, auto-play toggle, rainbow border animation, and mobile optimization',
     new_0_5_6_2: 'Add robust LLM JSON parser with tolerance for Python format and extract text from streaming events',
diff --git a/packages/client/src/i18n/locales/es.ts b/packages/client/src/i18n/locales/es.ts
index 582be38..ccd7339 100644
--- a/packages/client/src/i18n/locales/es.ts
+++ b/packages/client/src/i18n/locales/es.ts
@@ -872,6 +872,7 @@ jobTriggered: 'Job ejecutado',
     new_0_5_23_3: 'Isolate gateway profile environment variables to prevent credentials leaking across profiles',
     new_0_5_23_4: 'Reserve the Web UI port during gateway allocation to avoid startup conflicts',
     new_0_5_23_5: 'Fix self-update restart handling so successful helper exits are not reported as failures',
+    new_0_5_24_1: 'Align Bridge chat with API Server handling for multimodal input, system prompt, and workspace context',
     new_0_5_5_1: '🎉 ¡Feliz Día del Trabajo! Hoy no se trabaja, agradezcan su comprensión',
     new_0_5_5_2: 'Añadida página de historial para sesiones Hermes',
     new_0_5_5_3: 'La página de historial gestiona sesiones de forma independiente',
diff --git a/packages/client/src/i18n/locales/fr.ts b/packages/client/src/i18n/locales/fr.ts
index a864f72..e6a781c 100644
--- a/packages/client/src/i18n/locales/fr.ts
+++ b/packages/client/src/i18n/locales/fr.ts
@@ -871,6 +871,7 @@ jobTriggered: 'Job declenche',
     new_0_5_23_3: 'Isolate gateway profile environment variables to prevent credentials leaking across profiles',
     new_0_5_23_4: 'Reserve the Web UI port during gateway allocation to avoid startup conflicts',
     new_0_5_23_5: 'Fix self-update restart handling so successful helper exits are not reported as failures',
+    new_0_5_24_1: 'Align Bridge chat with API Server handling for multimodal input, system prompt, and workspace context',
     new_0_5_5_1: '🎉 Joyeuse Fête du Travail! Pas de travail aujourd\'hui, merci de votre compréhension',
     new_0_5_5_2: 'Ajout d\'une page d\'historique pour les sessions Hermes',
     new_0_5_5_3: 'La page d\'historique gère les sessions de manière indépendante',
diff --git a/packages/client/src/i18n/locales/ja.ts b/packages/client/src/i18n/locales/ja.ts
index a936806..0948510 100644
--- a/packages/client/src/i18n/locales/ja.ts
+++ b/packages/client/src/i18n/locales/ja.ts
@@ -872,6 +872,7 @@ export default {
     new_0_5_23_3: 'Isolate gateway profile environment variables to prevent credentials leaking across profiles',
     new_0_5_23_4: 'Reserve the Web UI port during gateway allocation to avoid startup conflicts',
     new_0_5_23_5: 'Fix self-update restart handling so successful helper exits are not reported as failures',
+    new_0_5_24_1: 'Align Bridge chat with API Server handling for multimodal input, system prompt, and workspace context',
     new_0_5_5_1: '🎉 労働者の日！今日はお休みです、何卒ご理解ください',
     new_0_5_5_2: 'Hermesセッション履歴ページを追加',
     new_0_5_5_3: '履歴ページはアクティブチャットに干渉せずにセッション管理',
diff --git a/packages/client/src/i18n/locales/ko.ts b/packages/client/src/i18n/locales/ko.ts
index c894db7..7c968a7 100644
--- a/packages/client/src/i18n/locales/ko.ts
+++ b/packages/client/src/i18n/locales/ko.ts
@@ -872,6 +872,7 @@ export default {
     new_0_5_23_3: 'Isolate gateway profile environment variables to prevent credentials leaking across profiles',
     new_0_5_23_4: 'Reserve the Web UI port during gateway allocation to avoid startup conflicts',
     new_0_5_23_5: 'Fix self-update restart handling so successful helper exits are not reported as failures',
+    new_0_5_24_1: 'Align Bridge chat with API Server handling for multimodal input, system prompt, and workspace context',
     new_0_5_5_1: '🎉 노동절 감사합니다! 오늘은 쉬니까 양해 부탁드립니다',
     new_0_5_5_2: 'Hermes 세션 기록 페이지 추가',
     new_0_5_5_3: '기록 페이지는 독립적으로 세션 관리',
diff --git a/packages/client/src/i18n/locales/pt.ts b/packages/client/src/i18n/locales/pt.ts
index ea16e32..22ba837 100644
--- a/packages/client/src/i18n/locales/pt.ts
+++ b/packages/client/src/i18n/locales/pt.ts
@@ -872,6 +872,7 @@ jobTriggered: 'Job acionado',
     new_0_5_23_3: 'Isolate gateway profile environment variables to prevent credentials leaking across profiles',
     new_0_5_23_4: 'Reserve the Web UI port during gateway allocation to avoid startup conflicts',
     new_0_5_23_5: 'Fix self-update restart handling so successful helper exits are not reported as failures',
+    new_0_5_24_1: 'Align Bridge chat with API Server handling for multimodal input, system prompt, and workspace context',
     new_0_5_5_1: '🎉 Feliz Dia do Trabalhador! Hoje não se trabalha, obrigado pela compreensão',
     new_0_5_5_2: 'Adicionada página de histórico para sessões Hermes',
     new_0_5_5_3: 'Página de histórico gerencia sessões de forma independente',
diff --git a/packages/client/src/i18n/locales/zh-TW.ts b/packages/client/src/i18n/locales/zh-TW.ts
index 45b9b9d..58e898c 100644
--- a/packages/client/src/i18n/locales/zh-TW.ts
+++ b/packages/client/src/i18n/locales/zh-TW.ts
@@ -1155,6 +1155,7 @@ export default {
     new_0_5_23_3: '隔離 gateway profile 環境變數，防止憑證在不同 profile 之間串用',
     new_0_5_23_4: 'gateway 分配連接埠時保留 Web UI 連接埠，避免啟動連接埠衝突',
     new_0_5_23_5: '修復自更新重啟邏輯，避免將 restart helper 的成功退出誤報為失敗',
+    new_0_5_24_1: '對齊 Bridge 聊天與 API Server 的多模態輸入、系統提示詞和工作區上下文處理',
     new_0_5_6_1: '新增語音播放功能：使用 Web Speech API，支援手動播放按鈕、自動播放開關、彩虹邊框動畫和行動端最佳化',
     new_0_5_6_2: '新增強健的 LLM JSON 解析器，相容 Python 格式並從串流事件中擷取文字',
     new_0_5_6_3: 'Skills 功能增強：使用統計、來源過濾、封存技能、來源追溯和釘選切換',
diff --git a/packages/client/src/i18n/locales/zh.ts b/packages/client/src/i18n/locales/zh.ts
index d242a2d..42ef92f 100644
--- a/packages/client/src/i18n/locales/zh.ts
+++ b/packages/client/src/i18n/locales/zh.ts
@@ -1155,6 +1155,7 @@ export default {
     new_0_5_23_3: '隔离 gateway profile 环境变量，防止凭据在不同 profile 之间串用',
     new_0_5_23_4: 'gateway 分配端口时保留 Web UI 端口，避免启动端口冲突',
     new_0_5_23_5: '修复自更新重启逻辑，避免将 restart helper 的成功退出误报为失败',
+    new_0_5_24_1: '对齐 Bridge 聊天与 API Server 的多模态输入、系统提示词和工作区上下文处理',
 
     new_0_5_6_1: '新增语音播放功能：使用 Web Speech API，支持手动播放按钮、自动播放开关、彩虹边框动画和移动端优化',
     new_0_5_6_2: '新增健壮的 LLM JSON 解析器，兼容 Python 格式并从流式事件中提取文本',
diff --git a/packages/server/src/services/hermes/run-chat/content-blocks.ts b/packages/server/src/services/hermes/run-chat/content-blocks.ts
index 484b42d..9f5b7eb 100644
--- a/packages/server/src/services/hermes/run-chat/content-blocks.ts
+++ b/packages/server/src/services/hermes/run-chat/content-blocks.ts
@@ -54,3 +54,20 @@ export async function convertContentBlocks(blocks: ContentBlock[]): Promise<Arra
 
   return parts
 }
+
+/**
+ * Convert ContentBlock[] to the normalized multimodal shape Hermes agent
+ * receives after /v1/responses input normalization.
+ */
+export async function convertContentBlocksForAgent(blocks: ContentBlock[]): Promise<Array<{ type: string; text?: string; image_url?: { url: string } }>> {
+  const responseParts = await convertContentBlocks(blocks)
+  return responseParts.map((part) => {
+    if (part.type === 'input_text') {
+      return { type: 'text', text: part.text || '' }
+    }
+    if (part.type === 'input_image') {
+      return { type: 'image_url', image_url: { url: part.image_url || '' } }
+    }
+    return { type: 'text', text: part.text || '' }
+  })
+}
diff --git a/packages/server/src/services/hermes/run-chat/handle-bridge-run.ts b/packages/server/src/services/hermes/run-chat/handle-bridge-run.ts
index ffe8f3b..416e4af 100644
--- a/packages/server/src/services/hermes/run-chat/handle-bridge-run.ts
+++ b/packages/server/src/services/hermes/run-chat/handle-bridge-run.ts
@@ -4,11 +4,12 @@
  */
 
 import type { Server, Socket } from 'socket.io'
+import { getSystemPrompt } from '../../../lib/llm-prompt'
 import { getSession, createSession, addMessage, updateSessionStats } from '../../../db/hermes/session-store'
 import { updateUsage } from '../../../db/hermes/usage-store'
 import { logger, bridgeLogger } from '../../logger'
 import { AgentBridgeClient, type AgentBridgeMessage, type AgentBridgeOutput } from '../agent-bridge'
-import { contentBlocksToString, extractTextForPreview } from './content-blocks'
+import { contentBlocksToString, convertContentBlocksForAgent, extractTextForPreview, isContentBlockArray } from './content-blocks'
 import { buildCompressedHistory } from './compression'
 import { pushState, replaceState } from './compression'
 import { calcAndUpdateUsage, estimateUsageTokensFromMessages } from './usage'
@@ -22,6 +23,7 @@ import {
 import { forceCompressBridgeHistory } from './compression'
 import { summarizeToolArguments } from './response-utils'
 import { buildDbHistory } from './compression'
+import { convertHistoryFormat } from './message-format'
 import type { ContentBlock, SessionState } from './types'
 import type { ChatMessage } from '../../../lib/context-compressor'
 
@@ -45,6 +47,15 @@ export async function handleBridgeRun(
     return
   }
 
+  let fullInstructions = instructions
+    ? `${getSystemPrompt()}\n${instructions}`
+    : getSystemPrompt()
+  const sessionRow = getSession(session_id)
+  if (sessionRow?.workspace) {
+    const workspaceCtx = `[Current working directory: ${sessionRow.workspace}]`
+    fullInstructions = `\n${workspaceCtx}\n${fullInstructions}`
+  }
+
   const runMarker = `cli_run_${Date.now().toString(36)}_${Math.random().toString(36).slice(2, 8)}`
   const now = Math.floor(Date.now() / 1000)
   let state = sessionMap.get(session_id)
@@ -107,17 +118,22 @@ export async function handleBridgeRun(
     emit,
     sessionMap,
   )
+  const bridgeHistory = history.length > 0 ? convertHistoryFormat(history) : history
 
   try {
+    const bridgeInput = isContentBlockArray(input)
+      ? await convertContentBlocksForAgent(input)
+      : input
     logger.info('[chat-run-socket] starting CLI bridge run for session %s', session_id)
     bridgeLogger.info({
       sessionId: session_id,
       profile,
       inputChars: inputStr.length,
       historyMessages: history.length,
-      hasInstructions: Boolean(instructions),
+      hasInstructions: Boolean(fullInstructions),
+      multimodalInput: isContentBlockArray(input),
     }, '[chat-run-socket] starting CLI bridge run')
-    const started = await bridge.chat(session_id, input as AgentBridgeMessage, history, instructions, profile)
+    const started = await bridge.chat(session_id, bridgeInput as AgentBridgeMessage, bridgeHistory, fullInstructions, profile)
     state.runId = started.run_id
     bridgeLogger.info({
       sessionId: session_id,