diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index 3e054ce7d2..377f10bf64 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -1905,6 +1905,7 @@ export class ClineProvider
 			terminalCompressProgressBar,
 			historyPreviewCollapsed,
 			reasoningBlockCollapsed,
+			requireCtrlEnterToSend,
 			cloudUserInfo,
 			cloudIsAuthenticated,
 			sharingEnabled,
@@ -2058,6 +2059,7 @@ export class ClineProvider
 			hasSystemPromptOverride,
 			historyPreviewCollapsed: historyPreviewCollapsed ?? false,
 			reasoningBlockCollapsed: reasoningBlockCollapsed ?? true,
+			requireCtrlEnterToSend: requireCtrlEnterToSend ?? false,
 			cloudUserInfo,
 			cloudIsAuthenticated: cloudIsAuthenticated ?? false,
 			cloudOrganizations,
@@ -2287,6 +2289,7 @@ export class ClineProvider
 			maxConcurrentFileReads: stateValues.maxConcurrentFileReads ?? 5,
 			historyPreviewCollapsed: stateValues.historyPreviewCollapsed ?? false,
 			reasoningBlockCollapsed: stateValues.reasoningBlockCollapsed ?? true,
+			requireCtrlEnterToSend: stateValues.requireCtrlEnterToSend ?? false,
 			cloudUserInfo,
 			cloudIsAuthenticated,
 			sharingEnabled,
diff --git a/src/shared/ExtensionMessage.ts b/src/shared/ExtensionMessage.ts
index 2535a78832..e892c72075 100644
--- a/src/shared/ExtensionMessage.ts
+++ b/src/shared/ExtensionMessage.ts
@@ -131,6 +131,7 @@ export interface ExtensionMessage {
 		| "interactionRequired"
 		| "browserSessionUpdate"
 		| "browserSessionNavigate"
+		| "requireCtrlEnterToSend"
 	text?: string
 	payload?: any // Add a generic payload for now, can refine later
 	// Checkpoint warning message
@@ -138,6 +139,7 @@ export interface ExtensionMessage {
 		type: "WAIT_TIMEOUT" | "INIT_TIMEOUT"
 		timeout: number
 	}
+	bool?: boolean
 	action?:
 		| "chatButtonClicked"
 		| "settingsButtonClicked"
@@ -239,7 +241,6 @@ export type ExtensionState = Pick<
 	| "alwaysAllowFollowupQuestions"
 	| "alwaysAllowExecute"
 	| "alwaysAllowUpdateTodoList"
-	| "requireCtrlEnterToSend"
 	| "followupAutoApproveTimeoutMs"
 	| "allowedCommands"
 	| "deniedCommands"
@@ -289,6 +290,7 @@ export type ExtensionState = Pick<
 	| "includeCurrentTime"
 	| "includeCurrentCost"
 	| "maxGitStatusFiles"
+	| "requireCtrlEnterToSend"
 > & {
 	version: string
 	clineMessages: ClineMessage[]
diff --git a/webview-ui/src/context/ExtensionStateContext.tsx b/webview-ui/src/context/ExtensionStateContext.tsx
index c96d0541e9..af80d4b174 100644
--- a/webview-ui/src/context/ExtensionStateContext.tsx
+++ b/webview-ui/src/context/ExtensionStateContext.tsx
@@ -275,7 +275,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		alwaysAllowUpdateTodoList: true,
 		includeDiagnosticMessages: true,
 		maxDiagnosticMessages: 50,
-		requireCtrlEnterToSend: false,
+		requireCtrlEnterToSend: false, // Default to expected value
 		openRouterImageApiKey: "",
 		openRouterImageGenerationSelectedModel: "",
 		includeCurrentTime: true,
@@ -425,6 +425,10 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 					}
 					break
 				}
+				case "requireCtrlEnterToSend": {
+					setState((prevState) => ({ ...prevState, requireCtrlEnterToSend: message.bool ?? false }))
+					break
+				}
 			}
 		},
 		[setListApiConfigMeta],