diff --git a/backend/open_webui/config.py b/backend/open_webui/config.py
index ec541f5a336..3cb594bdf31 100644
--- a/backend/open_webui/config.py
+++ b/backend/open_webui/config.py
@@ -2296,6 +2296,32 @@ class BannerModel(BaseModel):
 </chat_history>
 """
 
+# Retrieval (knowledge base) queries need a different prompt than web search queries:
+# semantic vector search rewards natural-language phrasings over keyword queries.
+RETRIEVAL_QUERY_GENERATION_PROMPT_TEMPLATE = os.getenv('RETRIEVAL_QUERY_GENERATION_PROMPT_TEMPLATE', '')
+
+DEFAULT_RETRIEVAL_QUERY_GENERATION_PROMPT_TEMPLATE = """### Task:
+Analyze the chat history and generate 1-3 search queries optimized for retrieving relevant documents from a knowledge base using semantic vector search.
+
+### Guidelines:
+- Respond **EXCLUSIVELY** with a JSON object.
+- Base queries on the **user's questions and information needs only**. Use assistant responses solely for context and disambiguation (e.g. resolving "that", "it", "the one you mentioned").
+- Generate queries as natural-language phrases that capture the semantic meaning of the user's information need.
+- Reformulate conversational references into standalone, self-contained queries.
+- Each query should target a different aspect or angle to maximize retrieval coverage.
+- If the user's message clearly needs no document retrieval (e.g. greetings), return: { "queries": [] }
+- Respond in the same language as the user's messages.
+- Today's date is: {{CURRENT_DATE}}
+
+### Output:
+{ "queries": ["query1", "query2"] }
+
+### Chat History:
+<chat_history>
+{{MESSAGES:END:4}}
+</chat_history>
+"""
+
 ENABLE_AUTOCOMPLETE_GENERATION = os.getenv('ENABLE_AUTOCOMPLETE_GENERATION', 'False').lower() == 'true'
 
 AUTOCOMPLETE_GENERATION_INPUT_MAX_LENGTH = int(os.getenv('AUTOCOMPLETE_GENERATION_INPUT_MAX_LENGTH', '-1'))
@@ -3101,6 +3127,7 @@ def feishu_oauth_register(oauth: OAuth):
     'task.query.search.enable': ENABLE_SEARCH_QUERY_GENERATION,
     'task.query.retrieval.enable': ENABLE_RETRIEVAL_QUERY_GENERATION,
     'task.query.prompt_template': QUERY_GENERATION_PROMPT_TEMPLATE,
+    'task.query.retrieval_prompt_template': RETRIEVAL_QUERY_GENERATION_PROMPT_TEMPLATE,
     'task.autocomplete.enable': ENABLE_AUTOCOMPLETE_GENERATION,
     'task.autocomplete.input_max_length': AUTOCOMPLETE_GENERATION_INPUT_MAX_LENGTH,
     'task.autocomplete.prompt_template': AUTOCOMPLETE_GENERATION_PROMPT_TEMPLATE,
diff --git a/backend/open_webui/routers/tasks.py b/backend/open_webui/routers/tasks.py
index 4e377e2b789..3bf6afdb96d 100644
--- a/backend/open_webui/routers/tasks.py
+++ b/backend/open_webui/routers/tasks.py
@@ -11,6 +11,7 @@
     DEFAULT_IMAGE_PROMPT_GENERATION_PROMPT_TEMPLATE,
     DEFAULT_MOA_GENERATION_PROMPT_TEMPLATE,
     DEFAULT_QUERY_GENERATION_PROMPT_TEMPLATE,
+    DEFAULT_RETRIEVAL_QUERY_GENERATION_PROMPT_TEMPLATE,
     DEFAULT_TAGS_GENERATION_PROMPT_TEMPLATE,
     DEFAULT_TITLE_GENERATION_PROMPT_TEMPLATE,
     DEFAULT_VOICE_MODE_PROMPT_TEMPLATE,
@@ -53,6 +54,7 @@
     'ENABLE_SEARCH_QUERY_GENERATION': 'task.query.search.enable',
     'ENABLE_RETRIEVAL_QUERY_GENERATION': 'task.query.retrieval.enable',
     'QUERY_GENERATION_PROMPT_TEMPLATE': 'task.query.prompt_template',
+    'RETRIEVAL_QUERY_GENERATION_PROMPT_TEMPLATE': 'task.query.retrieval_prompt_template',
     'TOOLS_FUNCTION_CALLING_PROMPT_TEMPLATE': 'task.tools.prompt_template',
     'ENABLE_VOICE_MODE_PROMPT': 'task.voice.prompt.enable',
     'VOICE_MODE_PROMPT_TEMPLATE': 'task.voice.prompt_template',
@@ -96,6 +98,7 @@ class TaskConfigForm(BaseModel):
     ENABLE_SEARCH_QUERY_GENERATION: bool
     ENABLE_RETRIEVAL_QUERY_GENERATION: bool
     QUERY_GENERATION_PROMPT_TEMPLATE: str
+    RETRIEVAL_QUERY_GENERATION_PROMPT_TEMPLATE: str
     TOOLS_FUNCTION_CALLING_PROMPT_TEMPLATE: str
     ENABLE_VOICE_MODE_PROMPT: bool
     VOICE_MODE_PROMPT_TEMPLATE: Optional[str]
@@ -441,11 +444,18 @@ async def generate_queries(request: Request, form_data: dict, user=Depends(get_v
 
     log.debug(f'generating {type} queries using model {task_model_id} for user {user.email}')
 
-    query_template = await Config.get('task.query.prompt_template')
-    if query_template.strip() != '':
-        template = query_template
+    if type == 'retrieval':
+        retrieval_query_template = await Config.get('task.query.retrieval_prompt_template')
+        if retrieval_query_template.strip() != '':
+            template = retrieval_query_template
+        else:
+            template = DEFAULT_RETRIEVAL_QUERY_GENERATION_PROMPT_TEMPLATE
     else:
-        template = DEFAULT_QUERY_GENERATION_PROMPT_TEMPLATE
+        query_template = await Config.get('task.query.prompt_template')
+        if query_template.strip() != '':
+            template = query_template
+        else:
+            template = DEFAULT_QUERY_GENERATION_PROMPT_TEMPLATE
 
     content = await query_generation_template(template, form_data['messages'], user)
 
diff --git a/src/lib/components/admin/Settings/Documents.svelte b/src/lib/components/admin/Settings/Documents.svelte
index 3f2911ff36c..2dfd88c2db1 100644
--- a/src/lib/components/admin/Settings/Documents.svelte
+++ b/src/lib/components/admin/Settings/Documents.svelte
@@ -17,6 +17,8 @@
 		updateRAGConfig
 	} from '$lib/apis/retrieval';
 
+	import { getTaskConfig, updateTaskConfig } from '$lib/apis';
+
 	import { reindexKnowledgeFiles } from '$lib/apis/knowledge';
 	import { deleteAllFiles } from '$lib/apis/files';
 
@@ -70,6 +72,8 @@
 	};
 
 	let RAGConfig: any = null;
+	let retrievalQueryPrompt: any = '';
+
 	const inputClass =
 		'w-full h-7 rounded-lg border border-gray-100/50 bg-gray-50/40 px-2 text-xs text-gray-700 outline-hidden transition-colors placeholder:text-gray-300 focus:border-blue-400 dark:border-white/[0.04] dark:bg-white/[0.03] dark:text-gray-300 dark:placeholder:text-gray-700 dark:focus:border-blue-500';
 	const actionButtonClass =
@@ -252,6 +256,15 @@
 			}
 		}
 
+		// Save the retrieval query prompt via the task config API
+		const currentTaskConfig = await getTaskConfig(localStorage.token);
+		if (currentTaskConfig) {
+			await updateTaskConfig(localStorage.token, {
+				...currentTaskConfig,
+				RETRIEVAL_QUERY_GENERATION_PROMPT_TEMPLATE: retrievalQueryPrompt
+			});
+		}
+
 		const res = await updateRAGConfig(localStorage.token, {
 			...RAGConfig,
 			// Convert null (from cleared number inputs) to empty string so the backend
@@ -340,6 +353,11 @@
 		config.RAG_TOKENIZER_MODEL = config?.RAG_TOKENIZER_MODEL ?? '';
 
 		RAGConfig = config;
+
+		const taskConfig = await getTaskConfig(localStorage.token);
+		if (taskConfig) {
+			retrievalQueryPrompt = taskConfig.RETRIEVAL_QUERY_GENERATION_PROMPT_TEMPLATE ?? '';
+		}
 	});
 </script>
 
@@ -1369,6 +1387,25 @@
 					{/if}
 				{/if}
 
+				<AdminSettingField
+					label={$i18n.t('Retrieval Query Generation Prompt')}
+					description={$i18n.t('Prompt template used when search query retrieved context is injected.')}
+				>
+					<Tooltip
+						content={$i18n.t('Leave empty to use the default prompt, or enter a custom prompt')}
+						placement="top-start"
+						className="w-full"
+					>
+						<Textarea
+							className={textareaClass}
+							bind:value={retrievalQueryPrompt}
+							placeholder={$i18n.t(
+								'Leave empty to use the default prompt, or enter a custom prompt'
+							)}
+						/>
+					</Tooltip>
+				</AdminSettingField>
+
 				<AdminSettingField
 					label={$i18n.t('RAG Template')}
 					description={$i18n.t('Prompt template used when retrieved context is injected.')}
diff --git a/src/lib/components/admin/Settings/Interface.svelte b/src/lib/components/admin/Settings/Interface.svelte
index c1cae4b83b7..57e844ef9cc 100644
--- a/src/lib/components/admin/Settings/Interface.svelte
+++ b/src/lib/components/admin/Settings/Interface.svelte
@@ -35,6 +35,7 @@
 		ENABLE_SEARCH_QUERY_GENERATION: true,
 		ENABLE_RETRIEVAL_QUERY_GENERATION: true,
 		QUERY_GENERATION_PROMPT_TEMPLATE: '',
+		RETRIEVAL_QUERY_GENERATION_PROMPT_TEMPLATE: '',
 		TOOLS_FUNCTION_CALLING_PROMPT_TEMPLATE: '',
 		ENABLE_VOICE_MODE_PROMPT: true,
 		VOICE_MODE_PROMPT_TEMPLATE: ''