diff --git a/src/core/prompts/tools/index.ts b/src/core/prompts/tools/index.ts
index d455abb8d7..b87c8c0724 100644
--- a/src/core/prompts/tools/index.ts
+++ b/src/core/prompts/tools/index.ts
@@ -118,6 +118,11 @@ export function getToolDescriptionsForMode(
 		tools.delete("update_todo_list")
 	}
 
+	// Conditionally exclude ask_followup_question if disabled in settings
+	if (settings?.alwaysAllowFollowupQuestions === false) {
+		tools.delete("ask_followup_question")
+	}
+
 	// Map tool descriptions for allowed tools
 	const descriptions = Array.from(tools).map((toolName) => {
 		const descriptionFn = toolDescriptionMap[toolName]
diff --git a/src/core/prompts/types.ts b/src/core/prompts/types.ts
index 3977ea98c5..875c38e931 100644
--- a/src/core/prompts/types.ts
+++ b/src/core/prompts/types.ts
@@ -5,4 +5,5 @@ export interface SystemPromptSettings {
 	maxConcurrentFileReads: number
 	todoListEnabled: boolean
 	useAgentRules: boolean
+	alwaysAllowFollowupQuestions: boolean
 }
diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index 5e96b6fb16..7770589c38 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -1898,6 +1898,7 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 			maxConcurrentFileReads,
 			maxReadFileLine,
 			apiConfiguration,
+			alwaysAllowFollowupQuestions,
 		} = state ?? {}
 
 		return await (async () => {
@@ -1928,6 +1929,7 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 					maxConcurrentFileReads: maxConcurrentFileReads ?? 5,
 					todoListEnabled: apiConfiguration?.todoListEnabled ?? true,
 					useAgentRules: vscode.workspace.getConfiguration("roo-cline").get<boolean>("useAgentRules") ?? true,
+					alwaysAllowFollowupQuestions: alwaysAllowFollowupQuestions ?? true,
 				},
 			)
 		})()
diff --git a/src/core/webview/generateSystemPrompt.ts b/src/core/webview/generateSystemPrompt.ts
index b8e87a1d4a..321a3b398d 100644
--- a/src/core/webview/generateSystemPrompt.ts
+++ b/src/core/webview/generateSystemPrompt.ts
@@ -25,6 +25,7 @@ export const generateSystemPrompt = async (provider: ClineProvider, message: Web
 		language,
 		maxReadFileLine,
 		maxConcurrentFileReads,
+		alwaysAllowFollowupQuestions,
 	} = await provider.getState()
 
 	// Check experiment to determine which diff strategy to use
@@ -85,6 +86,7 @@ export const generateSystemPrompt = async (provider: ClineProvider, message: Web
 			maxConcurrentFileReads: maxConcurrentFileReads ?? 5,
 			todoListEnabled: apiConfiguration?.todoListEnabled ?? true,
 			useAgentRules: vscode.workspace.getConfiguration("roo-cline").get<boolean>("useAgentRules") ?? true,
+			alwaysAllowFollowupQuestions: alwaysAllowFollowupQuestions ?? true,
 		},
 	)
 
diff --git a/webview-ui/src/i18n/locales/en/settings.json b/webview-ui/src/i18n/locales/en/settings.json
index eb893d6c51..7c6bce9951 100644
--- a/webview-ui/src/i18n/locales/en/settings.json
+++ b/webview-ui/src/i18n/locales/en/settings.json
@@ -172,7 +172,7 @@
 		},
 		"followupQuestions": {
 			"label": "Question",
-			"description": "Automatically select the first suggested answer for follow-up questions after the configured timeout",
+			"description": "Allow the AI to ask follow-up questions. When disabled, the AI will not have access to the question-asking tool and must proceed without clarification",
 			"timeoutLabel": "Time to wait before auto-selecting the first answer"
 		},
 		"execute": {