diff --git a/packages/types/src/global-settings.ts b/packages/types/src/global-settings.ts
index 579356ae2d45..464ee482014f 100644
--- a/packages/types/src/global-settings.ts
+++ b/packages/types/src/global-settings.ts
@@ -82,6 +82,7 @@ export const globalSettingsSchema = z.object({
 	alwaysAllowFollowupQuestions: z.boolean().optional(),
 	followupAutoApproveTimeoutMs: z.number().optional(),
 	alwaysAllowUpdateTodoList: z.boolean().optional(),
+	requireCtrlEnterToSend: z.boolean().optional(),
 	allowedCommands: z.array(z.string()).optional(),
 	deniedCommands: z.array(z.string()).optional(),
 	commandExecutionTimeout: z.number().optional(),
diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index f73a36d445ee..7a7f3030d63b 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -1858,6 +1858,7 @@ export class ClineProvider
 			terminalCompressProgressBar,
 			historyPreviewCollapsed,
 			reasoningBlockCollapsed,
+			requireCtrlEnterToSend,
 			cloudUserInfo,
 			cloudIsAuthenticated,
 			sharingEnabled,
@@ -1995,6 +1996,7 @@ export class ClineProvider
 			hasSystemPromptOverride,
 			historyPreviewCollapsed: historyPreviewCollapsed ?? false,
 			reasoningBlockCollapsed: reasoningBlockCollapsed ?? true,
+			requireCtrlEnterToSend: requireCtrlEnterToSend ?? false,
 			cloudUserInfo,
 			cloudIsAuthenticated: cloudIsAuthenticated ?? false,
 			cloudOrganizations,
@@ -2213,6 +2215,7 @@ 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/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index c06729674503..9cc44c5f9b76 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -1684,6 +1684,10 @@ export const webviewMessageHandler = async (
 			await updateGlobalState("reasoningBlockCollapsed", message.bool ?? true)
 			// No need to call postStateToWebview here as the UI already updated optimistically
 			break
+		case "requireCtrlEnterToSend":
+			await updateGlobalState("requireCtrlEnterToSend", message.bool)
+			// No need to call postStateToWebview here as the UI already updated optimistically
+			break
 		case "toggleApiConfigPin":
 			if (message.text) {
 				const currentPinned = getGlobalState("pinnedApiConfigs") ?? {}
diff --git a/src/shared/ExtensionMessage.ts b/src/shared/ExtensionMessage.ts
index 7d2759c91905..5082bd8a2e0f 100644
--- a/src/shared/ExtensionMessage.ts
+++ b/src/shared/ExtensionMessage.ts
@@ -127,6 +127,7 @@ export interface ExtensionMessage {
 		| "insertTextIntoTextarea"
 		| "dismissedUpsells"
 		| "organizationSwitchResult"
+		| "requireCtrlEnterToSend"
 	text?: string
 	payload?: any // Add a generic payload for now, can refine later
 	// Checkpoint warning message
@@ -134,6 +135,7 @@ export interface ExtensionMessage {
 		type: "WAIT_TIMEOUT" | "INIT_TIMEOUT"
 		timeout: number
 	}
+	bool?: boolean
 	action?:
 		| "chatButtonClicked"
 		| "mcpButtonClicked"
@@ -296,6 +298,7 @@ export type ExtensionState = Pick<
 	| "reasoningBlockCollapsed"
 	| "includeCurrentTime"
 	| "includeCurrentCost"
+	| "requireCtrlEnterToSend"
 > & {
 	version: string
 	clineMessages: ClineMessage[]
diff --git a/src/shared/WebviewMessage.ts b/src/shared/WebviewMessage.ts
index f10808cd428d..ecb0b449fdd5 100644
--- a/src/shared/WebviewMessage.ts
+++ b/src/shared/WebviewMessage.ts
@@ -199,6 +199,7 @@ export interface WebviewMessage {
 		| "profileThresholds"
 		| "setHistoryPreviewCollapsed"
 		| "setReasoningBlockCollapsed"
+		| "requireCtrlEnterToSend"
 		| "openExternal"
 		| "filterMarketplaceItems"
 		| "marketplaceButtonClicked"
diff --git a/webview-ui/src/components/chat/ChatTextArea.tsx b/webview-ui/src/components/chat/ChatTextArea.tsx
index c7813372fa79..e7a5d6f5adde 100644
--- a/webview-ui/src/components/chat/ChatTextArea.tsx
+++ b/webview-ui/src/components/chat/ChatTextArea.tsx
@@ -11,6 +11,7 @@ import { ExtensionMessage } from "@roo/ExtensionMessage"
 import { vscode } from "@src/utils/vscode"
 import { useExtensionState } from "@src/context/ExtensionStateContext"
 import { useAppTranslation } from "@src/i18n/TranslationContext"
+import { getSendMessageKeyCombination } from "@src/utils/platform"
 import {
 	ContextMenuOptionType,
 	getContextMenuOptions,
@@ -89,6 +90,7 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 			clineMessages,
 			commands,
 			cloudUserInfo,
+			requireCtrlEnterToSend,
 		} = useExtensionState()
 
 		// Find the ID and display text for the currently selected API configuration.
@@ -468,6 +470,11 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 				}
 
 				if (event.key === "Enter" && !event.shiftKey && !isComposing) {
+					// If Ctrl+Enter is required but neither Ctrl nor Meta (Cmd) key is pressed, don't send
+					if (requireCtrlEnterToSend && !event.ctrlKey && !event.metaKey) {
+						return
+					}
+
 					event.preventDefault()
 
 					// Always call onSend - let ChatView handle queueing when disabled
@@ -536,6 +543,7 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 				handleHistoryNavigation,
 				resetHistoryNavigation,
 				commands,
+				requireCtrlEnterToSend,
 			],
 		)
 
@@ -995,11 +1003,8 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 									"font-vscode-font-family",
 									"text-vscode-editor-font-size",
 									"leading-vscode-editor-line-height",
-									isFocused
-										? "border border-vscode-focusBorder outline outline-vscode-focusBorder"
-										: isDraggingOver
-											? "border-2 border-dashed border-vscode-focusBorder"
-											: "border border-transparent",
+									"border-none",
+									"outline-none",
 									"pl-2",
 									"py-2",
 									isEditMode ? "pr-20" : "pr-9",
@@ -1154,7 +1159,13 @@ export const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 										</button>
 									</StandardTooltip>
 								)}
-								<StandardTooltip content={t("chat:sendMessage")}>
+								<StandardTooltip
+									content={
+										requireCtrlEnterToSend
+											? t("chat:sendMessage") +
+												` (${t("chat:pressToSend", { keyCombination: getSendMessageKeyCombination() })})`
+											: t("chat:sendMessage")
+									}>
 									<button
 										aria-label={t("chat:sendMessage")}
 										disabled={false}
diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index 929fa9427aa0..765be57527f9 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -790,7 +790,8 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 				case "action":
 					switch (message.action!) {
 						case "didBecomeVisible":
-							if (!isHidden && !sendingDisabled && !enableButtons) {
+							// Do not grab focus during follow-up questions
+							if (!isHidden && !sendingDisabled && !enableButtons && clineAsk !== "followup") {
 								textAreaRef.current?.focus()
 							}
 							break
@@ -855,6 +856,7 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 			handlePrimaryButtonClick,
 			handleSecondaryButtonClick,
 			setCheckpointWarning,
+			clineAsk,
 		],
 	)
 
@@ -976,12 +978,13 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 
 	useDebounceEffect(
 		() => {
-			if (!isHidden && !sendingDisabled && !enableButtons) {
+			// Do not grab focus during follow-up questions
+			if (!isHidden && !sendingDisabled && !enableButtons && clineAsk !== "followup") {
 				textAreaRef.current?.focus()
 			}
 		},
 		50,
-		[isHidden, sendingDisabled, enableButtons],
+		[isHidden, sendingDisabled, enableButtons, clineAsk],
 	)
 
 	const isReadOnlyToolAction = useCallback((message: ClineMessage | undefined) => {
@@ -1516,7 +1519,8 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 					/>
 				)
 			}
-			const hasCheckpoint = modifiedMessages.some((message) => message.say === "checkpoint_saved")
+			// Lint: keep underscore to mark intentionally unused (prop removed)
+			const _hasCheckpoint = modifiedMessages.some((message) => message.say === "checkpoint_saved")
 
 			// regular message
 			return (
@@ -1524,12 +1528,12 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 					key={messageOrGroup.ts}
 					message={messageOrGroup}
 					isExpanded={expandedRows[messageOrGroup.ts] || false}
-					onToggleExpand={toggleRowExpansion} // This was already stabilized
-					lastModifiedMessage={modifiedMessages.at(-1)} // Original direct access
-					isLast={index === groupedMessages.length - 1} // Original direct access
+					onToggleExpand={toggleRowExpansion}
+					lastModifiedMessage={modifiedMessages.at(-1)}
+					isLast={index === groupedMessages.length - 1}
 					onHeightChange={handleRowHeightChange}
 					isStreaming={isStreaming}
-					onSuggestionClick={handleSuggestionClickInRow} // This was already stabilized
+					onSuggestionClick={handleSuggestionClickInRow}
 					onBatchFileResponse={handleBatchFileResponse}
 					onFollowUpUnmount={handleFollowUpUnmount}
 					isFollowUpAnswered={messageOrGroup.isAnswered === true || messageOrGroup.ts === currentFollowUpTs}
@@ -1551,7 +1555,6 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 							return tool.tool === "updateTodoList" && enableButtons && !!primaryButtonText
 						})()
 					}
-					hasCheckpoint={hasCheckpoint}
 				/>
 			)
 		},
diff --git a/webview-ui/src/components/chat/__tests__/ChatTextArea.spec.tsx b/webview-ui/src/components/chat/__tests__/ChatTextArea.spec.tsx
index af7704aa1b74..8732115221f9 100644
--- a/webview-ui/src/components/chat/__tests__/ChatTextArea.spec.tsx
+++ b/webview-ui/src/components/chat/__tests__/ChatTextArea.spec.tsx
@@ -1058,6 +1058,85 @@ describe("ChatTextArea", () => {
 		})
 	})
 
+	describe("keyboard handling with requireCtrlEnterToSend", () => {
+		beforeEach(() => {
+			;(useExtensionState as ReturnType<typeof vi.fn>).mockReturnValue({
+				filePaths: [],
+				openedTabs: [],
+				apiConfiguration: {
+					apiProvider: "anthropic",
+				},
+				taskHistory: [],
+				cwd: "/test/workspace",
+				requireCtrlEnterToSend: true,
+			})
+		})
+
+		it("should send message with Ctrl+Enter when requireCtrlEnterToSend is enabled", () => {
+			const onSend = vi.fn()
+			const { container } = render(<ChatTextArea {...defaultProps} onSend={onSend} inputValue="Test message" />)
+
+			const textarea = container.querySelector("textarea")!
+			fireEvent.keyDown(textarea, { key: "Enter", ctrlKey: true })
+
+			expect(onSend).toHaveBeenCalled()
+		})
+
+		it("should send message with Cmd+Enter when requireCtrlEnterToSend is enabled", () => {
+			const onSend = vi.fn()
+			const { container } = render(<ChatTextArea {...defaultProps} onSend={onSend} inputValue="Test message" />)
+
+			const textarea = container.querySelector("textarea")!
+			fireEvent.keyDown(textarea, { key: "Enter", metaKey: true })
+
+			expect(onSend).toHaveBeenCalled()
+		})
+
+		it("should not send message with regular Enter when requireCtrlEnterToSend is enabled", () => {
+			const onSend = vi.fn()
+			const { container } = render(<ChatTextArea {...defaultProps} onSend={onSend} inputValue="Test message" />)
+
+			const textarea = container.querySelector("textarea")!
+			fireEvent.keyDown(textarea, { key: "Enter" })
+
+			expect(onSend).not.toHaveBeenCalled()
+		})
+
+		it("should insert newline with Shift+Enter when requireCtrlEnterToSend is enabled", () => {
+			const setInputValue = vi.fn()
+			const { container } = render(
+				<ChatTextArea {...defaultProps} setInputValue={setInputValue} inputValue="Test message" />,
+			)
+
+			const textarea = container.querySelector("textarea")!
+			fireEvent.keyDown(textarea, { key: "Enter", shiftKey: true })
+
+			// Should not call onSend, allowing default behavior (insert newline)
+			expect(setInputValue).not.toHaveBeenCalled()
+		})
+
+		it("should send message with regular Enter when requireCtrlEnterToSend is disabled", () => {
+			;(useExtensionState as ReturnType<typeof vi.fn>).mockReturnValue({
+				filePaths: [],
+				openedTabs: [],
+				apiConfiguration: {
+					apiProvider: "anthropic",
+				},
+				taskHistory: [],
+				cwd: "/test/workspace",
+				requireCtrlEnterToSend: false,
+			})
+
+			const onSend = vi.fn()
+			const { container } = render(<ChatTextArea {...defaultProps} onSend={onSend} inputValue="Test message" />)
+
+			const textarea = container.querySelector("textarea")!
+			fireEvent.keyDown(textarea, { key: "Enter" })
+
+			expect(onSend).toHaveBeenCalled()
+		})
+	})
+
 	describe("send button visibility", () => {
 		it("should show send button when there are images but no text", () => {
 			const { container } = render(
diff --git a/webview-ui/src/components/settings/SettingsView.tsx b/webview-ui/src/components/settings/SettingsView.tsx
index 506eabc4cb50..43b484daa3ec 100644
--- a/webview-ui/src/components/settings/SettingsView.tsx
+++ b/webview-ui/src/components/settings/SettingsView.tsx
@@ -198,6 +198,7 @@ const SettingsView = forwardRef<SettingsViewRef, SettingsViewProps>(({ onDone, t
 		reasoningBlockCollapsed,
 		includeCurrentTime,
 		includeCurrentCost,
+		requireCtrlEnterToSend,
 	} = cachedState
 
 	const apiConfiguration = useMemo(() => cachedState.apiConfiguration ?? {}, [cachedState.apiConfiguration])
@@ -390,6 +391,7 @@ const SettingsView = forwardRef<SettingsViewRef, SettingsViewProps>(({ onDone, t
 			vscode.postMessage({ type: "setReasoningBlockCollapsed", bool: reasoningBlockCollapsed ?? true })
 			vscode.postMessage({ type: "includeCurrentTime", bool: includeCurrentTime ?? true })
 			vscode.postMessage({ type: "includeCurrentCost", bool: includeCurrentCost ?? true })
+			vscode.postMessage({ type: "requireCtrlEnterToSend", bool: requireCtrlEnterToSend ?? false })
 			vscode.postMessage({ type: "upsertApiConfiguration", text: currentApiConfigName, apiConfiguration })
 			vscode.postMessage({ type: "telemetrySetting", text: telemetrySetting })
 			vscode.postMessage({ type: "profileThresholds", values: profileThresholds })
@@ -791,6 +793,7 @@ const SettingsView = forwardRef<SettingsViewRef, SettingsViewProps>(({ onDone, t
 					{activeTab === "ui" && (
 						<UISettings
 							reasoningBlockCollapsed={reasoningBlockCollapsed ?? true}
+							requireCtrlEnterToSend={requireCtrlEnterToSend ?? false}
 							setCachedStateField={setCachedStateField}
 						/>
 					)}
diff --git a/webview-ui/src/components/settings/UISettings.tsx b/webview-ui/src/components/settings/UISettings.tsx
index 2de16e688224..ddc61fd449de 100644
--- a/webview-ui/src/components/settings/UISettings.tsx
+++ b/webview-ui/src/components/settings/UISettings.tsx
@@ -1,5 +1,6 @@
 import { HTMLAttributes } from "react"
 import { useAppTranslation } from "@/i18n/TranslationContext"
+import { getPrimaryModifierKey } from "@/utils/platform"
 import { VSCodeCheckbox } from "@vscode/webview-ui-toolkit/react"
 import { Glasses } from "lucide-react"
 import { telemetryClient } from "@/utils/TelemetryClient"
@@ -11,10 +12,16 @@ import { ExtensionStateContextType } from "@/context/ExtensionStateContext"
 
 interface UISettingsProps extends HTMLAttributes<HTMLDivElement> {
 	reasoningBlockCollapsed: boolean
+	requireCtrlEnterToSend?: boolean
 	setCachedStateField: SetCachedStateField<keyof ExtensionStateContextType>
 }
 
-export const UISettings = ({ reasoningBlockCollapsed, setCachedStateField, ...props }: UISettingsProps) => {
+export const UISettings = ({
+	reasoningBlockCollapsed,
+	requireCtrlEnterToSend,
+	setCachedStateField,
+	...props
+}: UISettingsProps) => {
 	const { t } = useAppTranslation()
 
 	const handleReasoningBlockCollapsedChange = (value: boolean) => {
@@ -26,6 +33,15 @@ export const UISettings = ({ reasoningBlockCollapsed, setCachedStateField, ...pr
 		})
 	}
 
+	const handleRequireCtrlEnterToSendChange = (value: boolean) => {
+		setCachedStateField("requireCtrlEnterToSend", value)
+
+		// Track telemetry event
+		telemetryClient.capture("ui_settings_ctrl_enter_changed", {
+			enabled: value,
+		})
+	}
+
 	return (
 		<div {...props}>
 			<SectionHeader>
@@ -49,6 +65,27 @@ export const UISettings = ({ reasoningBlockCollapsed, setCachedStateField, ...pr
 							{t("settings:ui.collapseThinking.description")}
 						</div>
 					</div>
+
+					{/* Require Ctrl+Enter to Send Setting */}
+					<div className="flex flex-col gap-1">
+						<VSCodeCheckbox
+							checked={requireCtrlEnterToSend ?? false}
+							onChange={(e: any) => handleRequireCtrlEnterToSendChange(e.target.checked)}
+							data-testid="ctrl-enter-checkbox">
+							<span className="font-medium">
+								{t("settings:ui.requireCtrlEnterToSend.label", {
+									primaryMod: getPrimaryModifierKey(),
+									interpolation: { prefix: "{", suffix: "}" },
+								})}
+							</span>
+						</VSCodeCheckbox>
+						<div className="text-vscode-descriptionForeground text-sm ml-5 mt-1">
+							{t("settings:ui.requireCtrlEnterToSend.description", {
+								primaryMod: getPrimaryModifierKey(),
+								interpolation: { prefix: "{", suffix: "}" },
+							})}
+						</div>
+					</div>
 				</div>
 			</Section>
 		</div>
diff --git a/webview-ui/src/context/ExtensionStateContext.tsx b/webview-ui/src/context/ExtensionStateContext.tsx
index 6443ccad93d5..9ed075e8d8ba 100644
--- a/webview-ui/src/context/ExtensionStateContext.tsx
+++ b/webview-ui/src/context/ExtensionStateContext.tsx
@@ -11,7 +11,6 @@ import {
 	type OrganizationAllowList,
 	type CloudOrganizationMembership,
 	ORGANIZATION_ALLOW_ALL,
-	DEFAULT_CHECKPOINT_TIMEOUT_SECONDS,
 } from "@roo-code/types"
 
 import { ExtensionMessage, ExtensionState, MarketplaceInstalledMetadata, Command } from "@roo/ExtensionMessage"
@@ -161,10 +160,12 @@ export interface ExtensionStateContextType extends ExtensionState {
 	setMaxDiagnosticMessages: (value: number) => void
 	includeTaskHistoryInEnhance?: boolean
 	setIncludeTaskHistoryInEnhance: (value: boolean) => void
-	includeCurrentTime?: boolean
+	includeCurrentTime: boolean
 	setIncludeCurrentTime: (value: boolean) => void
-	includeCurrentCost?: boolean
+	includeCurrentCost: boolean
 	setIncludeCurrentCost: (value: boolean) => void
+	requireCtrlEnterToSend: boolean
+	setRequireCtrlEnterToSend: (value: boolean) => void
 }
 
 export const ExtensionStateContext = createContext<ExtensionStateContextType | undefined>(undefined)
@@ -204,7 +205,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		ttsSpeed: 1.0,
 		diffEnabled: false,
 		enableCheckpoints: true,
-		checkpointTimeout: DEFAULT_CHECKPOINT_TIMEOUT_SECONDS, // Default to 15 seconds
+		checkpointTimeout: 15, // Default to 15 seconds
 		fuzzyMatchThreshold: 1.0,
 		language: "en", // Default language code
 		writeDelayMs: 1000,
@@ -272,6 +273,7 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		alwaysAllowUpdateTodoList: true,
 		includeDiagnosticMessages: true,
 		maxDiagnosticMessages: 50,
+		requireCtrlEnterToSend: false, // Default to expected value
 		openRouterImageApiKey: "",
 		openRouterImageGenerationSelectedModel: "",
 		includeCurrentTime: true,
@@ -421,6 +423,10 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 					}
 					break
 				}
+				case "requireCtrlEnterToSend": {
+					setState((prevState) => ({ ...prevState, requireCtrlEnterToSend: message.bool ?? false }))
+					break
+				}
 			}
 		},
 		[setListApiConfigMeta],
@@ -596,6 +602,10 @@ export const ExtensionStateContextProvider: React.FC<{ children: React.ReactNode
 		setIncludeCurrentTime,
 		includeCurrentCost,
 		setIncludeCurrentCost,
+		requireCtrlEnterToSend: !!state.requireCtrlEnterToSend,
+		setRequireCtrlEnterToSend: (value) => {
+			setState((prevState) => ({ ...prevState, requireCtrlEnterToSend: value }))
+		},
 	}
 
 	return <ExtensionStateContext.Provider value={contextValue}>{children}</ExtensionStateContext.Provider>
diff --git a/webview-ui/src/i18n/locales/ca/chat.json b/webview-ui/src/i18n/locales/ca/chat.json
index 16ea62c44390..2f8f6608f811 100644
--- a/webview-ui/src/i18n/locales/ca/chat.json
+++ b/webview-ui/src/i18n/locales/ca/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "Millora la sol·licitud amb context addicional",
 	"addImages": "Afegeix imatges al missatge",
 	"sendMessage": "Envia el missatge",
+	"pressToSend": "Prem {{keyCombination}} per enviar",
 	"stopTts": "Atura la síntesi de veu",
 	"typeMessage": "Escriu un missatge...",
 	"typeTask": "Escriu la teva tasca aquí...",
diff --git a/webview-ui/src/i18n/locales/ca/settings.json b/webview-ui/src/i18n/locales/ca/settings.json
index 20f693cfcae4..3eccb74777fb 100644
--- a/webview-ui/src/i18n/locales/ca/settings.json
+++ b/webview-ui/src/i18n/locales/ca/settings.json
@@ -901,6 +901,10 @@
 		"collapseThinking": {
 			"label": "Replega els missatges de pensament per defecte",
 			"description": "Quan estigui activat, els blocs de pensament es replegaran per defecte fins que interactuïs amb ells"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Requereix {primaryMod}+Enter per enviar missatges",
+			"description": "Quan estigui activat, hauràs de prémer {primaryMod}+Enter per enviar missatges en lloc de només Enter"
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/de/chat.json b/webview-ui/src/i18n/locales/de/chat.json
index a3f14d12549b..0c37115650ac 100644
--- a/webview-ui/src/i18n/locales/de/chat.json
+++ b/webview-ui/src/i18n/locales/de/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "Prompt mit zusätzlichem Kontext verbessern",
 	"addImages": "Bilder zur Nachricht hinzufügen",
 	"sendMessage": "Nachricht senden",
+	"pressToSend": "Drücke {{keyCombination}} zum Senden",
 	"stopTts": "Text-in-Sprache beenden",
 	"typeMessage": "Nachricht eingeben...",
 	"typeTask": "Gib deine Aufgabe hier ein...",
diff --git a/webview-ui/src/i18n/locales/de/settings.json b/webview-ui/src/i18n/locales/de/settings.json
index 3b7902812e35..394ee4400f00 100644
--- a/webview-ui/src/i18n/locales/de/settings.json
+++ b/webview-ui/src/i18n/locales/de/settings.json
@@ -901,6 +901,10 @@
 		"collapseThinking": {
 			"label": "Gedankenblöcke standardmäßig ausblenden",
 			"description": "Wenn aktiviert, werden Gedankenblöcke standardmäßig ausgeblendet, bis du mit ihnen interagierst"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Erfordert {primaryMod}+Enter zum Senden von Nachrichten",
+			"description": "Wenn aktiviert, musst du {primaryMod}+Enter drücken, um Nachrichten zu senden, anstatt nur Enter."
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/en/chat.json b/webview-ui/src/i18n/locales/en/chat.json
index 6f47f040c67b..932ea6a2e20a 100644
--- a/webview-ui/src/i18n/locales/en/chat.json
+++ b/webview-ui/src/i18n/locales/en/chat.json
@@ -130,6 +130,7 @@
 	"enhancePromptDescription": "The 'Enhance Prompt' button helps improve your prompt by providing additional context, clarification, or rephrasing. Try typing a prompt in here and clicking the button again to see how it works.",
 	"addImages": "Add images to message",
 	"sendMessage": "Send message",
+	"pressToSend": "Press {{keyCombination}} to send",
 	"stopTts": "Stop text-to-speech",
 	"typeMessage": "Type a message...",
 	"typeTask": "Type your task here...",
diff --git a/webview-ui/src/i18n/locales/en/settings.json b/webview-ui/src/i18n/locales/en/settings.json
index 950d4d2319f5..fad127b0e8b9 100644
--- a/webview-ui/src/i18n/locales/en/settings.json
+++ b/webview-ui/src/i18n/locales/en/settings.json
@@ -42,6 +42,10 @@
 		"collapseThinking": {
 			"label": "Collapse Thinking messages by default",
 			"description": "When enabled, thinking blocks will be collapsed by default until you interact with them"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Require {primaryMod}+Enter to send messages",
+			"description": "When enabled, you must press {primaryMod}+Enter to send messages instead of just Enter"
 		}
 	},
 	"prompts": {
diff --git a/webview-ui/src/i18n/locales/es/chat.json b/webview-ui/src/i18n/locales/es/chat.json
index e6084b371399..8fd787b8972b 100644
--- a/webview-ui/src/i18n/locales/es/chat.json
+++ b/webview-ui/src/i18n/locales/es/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "Mejorar el mensaje con contexto adicional",
 	"addImages": "Agregar imágenes al mensaje",
 	"sendMessage": "Enviar mensaje",
+	"pressToSend": "Presiona {{keyCombination}} para enviar",
 	"stopTts": "Detener texto a voz",
 	"typeMessage": "Escribe un mensaje...",
 	"typeTask": "Escribe tu tarea aquí...",
diff --git a/webview-ui/src/i18n/locales/es/settings.json b/webview-ui/src/i18n/locales/es/settings.json
index 24ba907958a3..3c05981fe084 100644
--- a/webview-ui/src/i18n/locales/es/settings.json
+++ b/webview-ui/src/i18n/locales/es/settings.json
@@ -901,6 +901,10 @@
 		"collapseThinking": {
 			"label": "Colapsar mensajes de pensamiento por defecto",
 			"description": "Cuando está activado, los bloques de pensamiento se colapsarán por defecto hasta que interactúes con ellos"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Requerir {primaryMod}+Enter para enviar mensajes",
+			"description": "Cuando está habilitado, debes presionar {primaryMod}+Enter para enviar mensajes en lugar de solo Enter"
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/fr/chat.json b/webview-ui/src/i18n/locales/fr/chat.json
index 38d63358ca98..5ec5fa8043c6 100644
--- a/webview-ui/src/i18n/locales/fr/chat.json
+++ b/webview-ui/src/i18n/locales/fr/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "Améliorer la requête avec un contexte supplémentaire",
 	"addImages": "Ajouter des images au message",
 	"sendMessage": "Envoyer le message",
+	"pressToSend": "Appuyez sur {{keyCombination}} pour envoyer",
 	"stopTts": "Arrêter la synthèse vocale",
 	"typeMessage": "Écrivez un message...",
 	"typeTask": "Écrivez votre tâche ici...",
diff --git a/webview-ui/src/i18n/locales/fr/settings.json b/webview-ui/src/i18n/locales/fr/settings.json
index fbcc6914d692..773ca88792e0 100644
--- a/webview-ui/src/i18n/locales/fr/settings.json
+++ b/webview-ui/src/i18n/locales/fr/settings.json
@@ -900,7 +900,11 @@
 	"ui": {
 		"collapseThinking": {
 			"label": "Réduire les messages de réflexion par défaut",
-			"description": "Si activé, les blocs de réflexion seront réduits par défaut jusqu'à ce que vous interagissiez avec eux"
+			"description": "Lorsque cette option est activée, les blocs de réflexion seront réduits par défaut jusqu'à ce que vous interagissiez avec eux"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Requiert {primaryMod}+Entrée pour envoyer des messages",
+			"description": "Lorsqu'activé, vous devez appuyer sur {primaryMod}+Entrée pour envoyer des messages au lieu de simplement Entrée"
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/hi/chat.json b/webview-ui/src/i18n/locales/hi/chat.json
index 9bc4b4619766..289dc82cefaf 100644
--- a/webview-ui/src/i18n/locales/hi/chat.json
+++ b/webview-ui/src/i18n/locales/hi/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "अतिरिक्त संदर्भ के साथ प्रॉम्प्ट बढ़ाएँ",
 	"addImages": "संदेश में चित्र जोड़ें",
 	"sendMessage": "संदेश भेजें",
+	"pressToSend": "दबाएं {{keyCombination}} भेजने के लिए",
 	"stopTts": "टेक्स्ट-टू-स्पीच बंद करें",
 	"typeMessage": "एक संदेश लिखें...",
 	"typeTask": "अपना कार्य यहां लिखें...",
diff --git a/webview-ui/src/i18n/locales/hi/settings.json b/webview-ui/src/i18n/locales/hi/settings.json
index a362fd301cdf..41cf4c5026d1 100644
--- a/webview-ui/src/i18n/locales/hi/settings.json
+++ b/webview-ui/src/i18n/locales/hi/settings.json
@@ -902,6 +902,10 @@
 		"collapseThinking": {
 			"label": "सोच संदेशों को डिफ़ॉल्ट रूप से संक्षिप्त करें",
 			"description": "सक्षम होने पर, सोच ब्लॉक आपके द्वारा उनके साथ इंटरैक्ट करने तक डिफ़ॉल्ट रूप से संक्षिप्त रहेंगे"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "संदेश भेजने के लिए {primaryMod}+Enter आवश्यक करें",
+			"description": "सक्षम होने पर, संदेश भेजने के लिए केवल Enter के बजाय {primaryMod}+Enter दबाना आवश्यक है"
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/id/chat.json b/webview-ui/src/i18n/locales/id/chat.json
index b61b47b3d884..e6a956fee701 100644
--- a/webview-ui/src/i18n/locales/id/chat.json
+++ b/webview-ui/src/i18n/locales/id/chat.json
@@ -133,6 +133,7 @@
 	},
 	"addImages": "Tambahkan gambar ke pesan",
 	"sendMessage": "Kirim pesan",
+	"pressToSend": "Tekan {{keyCombination}} untuk mengirim",
 	"stopTts": "Hentikan text-to-speech",
 	"typeMessage": "Ketik pesan...",
 	"typeTask": "Bangun, cari, tanya sesuatu",
diff --git a/webview-ui/src/i18n/locales/id/settings.json b/webview-ui/src/i18n/locales/id/settings.json
index aad93a749b09..6b308dbb7385 100644
--- a/webview-ui/src/i18n/locales/id/settings.json
+++ b/webview-ui/src/i18n/locales/id/settings.json
@@ -931,6 +931,10 @@
 		"collapseThinking": {
 			"label": "Ciutkan pesan Berpikir secara default",
 			"description": "Jika diaktifkan, blok berpikir akan diciutkan secara default sampai Anda berinteraksi dengannya"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Wajib {primaryMod}+Enter untuk mengirim pesan",
+			"description": "Saat aktif, Anda harus menekan {primaryMod}+Enter untuk mengirim pesan, bukan hanya Enter"
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/it/chat.json b/webview-ui/src/i18n/locales/it/chat.json
index 082c489e9313..2499fedbcabd 100644
--- a/webview-ui/src/i18n/locales/it/chat.json
+++ b/webview-ui/src/i18n/locales/it/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "Migliora prompt con contesto aggiuntivo",
 	"addImages": "Aggiungi immagini al messaggio",
 	"sendMessage": "Invia messaggio",
+	"pressToSend": "Premi {{keyCombination}} per inviare",
 	"stopTts": "Interrompi sintesi vocale",
 	"typeMessage": "Scrivi un messaggio...",
 	"typeTask": "Scrivi la tua attività qui...",
diff --git a/webview-ui/src/i18n/locales/it/settings.json b/webview-ui/src/i18n/locales/it/settings.json
index 63ed2b2f0462..722fa5d82180 100644
--- a/webview-ui/src/i18n/locales/it/settings.json
+++ b/webview-ui/src/i18n/locales/it/settings.json
@@ -901,7 +901,11 @@
 	"ui": {
 		"collapseThinking": {
 			"label": "Comprimi i messaggi di pensiero per impostazione predefinita",
-			"description": "Se abilitato, i blocchi di pensiero verranno compressi per impostazione predefinita finché non interagisci con essi"
+			"description": "Quando abilitato, i blocchi di pensiero saranno compressi per impostazione predefinita finché non interagisci con essi"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Richiedi {primaryMod}+Invio per inviare messaggi",
+			"description": "Quando abilitato, devi premere {primaryMod}+Invio per inviare messaggi invece di solo Invio"
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/ja/chat.json b/webview-ui/src/i18n/locales/ja/chat.json
index 531afc067e4d..d748a7b4d49c 100644
--- a/webview-ui/src/i18n/locales/ja/chat.json
+++ b/webview-ui/src/i18n/locales/ja/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "追加コンテキストでプロンプトを強化",
 	"addImages": "メッセージに画像を追加",
 	"sendMessage": "メッセージを送信",
+	"pressToSend": "{{keyCombination}} を押して送信",
 	"stopTts": "テキスト読み上げを停止",
 	"typeMessage": "メッセージを入力...",
 	"typeTask": "ここにタスクを入力...",
diff --git a/webview-ui/src/i18n/locales/ja/settings.json b/webview-ui/src/i18n/locales/ja/settings.json
index 84bf98c1e441..28a97b60fbdc 100644
--- a/webview-ui/src/i18n/locales/ja/settings.json
+++ b/webview-ui/src/i18n/locales/ja/settings.json
@@ -902,6 +902,10 @@
 		"collapseThinking": {
 			"label": "デフォルトで思考メッセージを折りたたむ",
 			"description": "有効にすると、操作するまで思考ブロックがデフォルトで折りたたまれます"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "メッセージ送信に{primaryMod}+Enterを必須にする",
+			"description": "有効にすると、Enterキーだけでなく{primaryMod}+Enterを押す必要があります"
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/ko/chat.json b/webview-ui/src/i18n/locales/ko/chat.json
index 9f7818bc4757..8201e6ce0102 100644
--- a/webview-ui/src/i18n/locales/ko/chat.json
+++ b/webview-ui/src/i18n/locales/ko/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "추가 컨텍스트로 프롬프트 향상",
 	"addImages": "메시지에 이미지 추가",
 	"sendMessage": "메시지 보내기",
+	"pressToSend": "{{keyCombination}}을(를) 눌러 보내기",
 	"stopTts": "텍스트 음성 변환 중지",
 	"typeMessage": "메시지 입력...",
 	"typeTask": "여기에 작업 입력...",
diff --git a/webview-ui/src/i18n/locales/ko/settings.json b/webview-ui/src/i18n/locales/ko/settings.json
index 3d7caa0ab101..799e25fd257e 100644
--- a/webview-ui/src/i18n/locales/ko/settings.json
+++ b/webview-ui/src/i18n/locales/ko/settings.json
@@ -902,6 +902,10 @@
 		"collapseThinking": {
 			"label": "기본적으로 생각 메시지 접기",
 			"description": "활성화하면 상호 작용할 때까지 생각 블록이 기본적으로 접힙니다"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "{primaryMod}+Enter를 눌러 메시지 보내기",
+			"description": "활성화하면 Enter 대신 {primaryMod}+Enter를 눌러 메시지를 보내야 합니다."
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/nl/chat.json b/webview-ui/src/i18n/locales/nl/chat.json
index 97380d370af0..f02560e48675 100644
--- a/webview-ui/src/i18n/locales/nl/chat.json
+++ b/webview-ui/src/i18n/locales/nl/chat.json
@@ -119,6 +119,7 @@
 	},
 	"addImages": "Afbeeldingen toevoegen aan bericht",
 	"sendMessage": "Bericht verzenden",
+	"pressToSend": "Druk op {{keyCombination}} om te verzenden",
 	"stopTts": "Stop tekst-naar-spraak",
 	"typeMessage": "Typ een bericht...",
 	"typeTask": "Typ hier je taak...",
diff --git a/webview-ui/src/i18n/locales/nl/settings.json b/webview-ui/src/i18n/locales/nl/settings.json
index 7ce4baefb924..72a5e20f56ee 100644
--- a/webview-ui/src/i18n/locales/nl/settings.json
+++ b/webview-ui/src/i18n/locales/nl/settings.json
@@ -902,6 +902,10 @@
 		"collapseThinking": {
 			"label": "Denkberichten standaard samenvouwen",
 			"description": "Indien ingeschakeld, worden denkblokken standaard samengevouwen totdat je ermee interageert"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Vereis {primaryMod}+Enter om berichten te verzenden",
+			"description": "Wanneer ingeschakeld, moet u {primaryMod}+Enter indrukken om berichten te verzenden in plaats van alleen Enter"
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/pl/chat.json b/webview-ui/src/i18n/locales/pl/chat.json
index 414262eaa7cf..2b0bca353e60 100644
--- a/webview-ui/src/i18n/locales/pl/chat.json
+++ b/webview-ui/src/i18n/locales/pl/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "Ulepsz podpowiedź dodatkowym kontekstem",
 	"addImages": "Dodaj obrazy do wiadomości",
 	"sendMessage": "Wyślij wiadomość",
+	"pressToSend": "Naciśnij {{keyCombination}}, aby wysłać",
 	"stopTts": "Zatrzymaj syntezę mowy",
 	"typeMessage": "Wpisz wiadomość...",
 	"typeTask": "Wpisz swoje zadanie tutaj...",
diff --git a/webview-ui/src/i18n/locales/pl/settings.json b/webview-ui/src/i18n/locales/pl/settings.json
index e1853ee53e43..56a11ca73626 100644
--- a/webview-ui/src/i18n/locales/pl/settings.json
+++ b/webview-ui/src/i18n/locales/pl/settings.json
@@ -902,6 +902,10 @@
 		"collapseThinking": {
 			"label": "Domyślnie zwijaj komunikaty o myśleniu",
 			"description": "Gdy włączone, bloki myślenia będą domyślnie zwinięte, dopóki nie wejdziesz z nimi w interakcję"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Wymaga {primaryMod}+Enter, aby wysłać wiadomości",
+			"description": "Po włączeniu musisz nacisnąć {primaryMod}+Enter, aby wysłać wiadomości zamiast tylko Enter."
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/pt-BR/chat.json b/webview-ui/src/i18n/locales/pt-BR/chat.json
index 0baa415bc7d3..64c9299d12f9 100644
--- a/webview-ui/src/i18n/locales/pt-BR/chat.json
+++ b/webview-ui/src/i18n/locales/pt-BR/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "Aprimorar prompt com contexto adicional",
 	"addImages": "Adicionar imagens à mensagem",
 	"sendMessage": "Enviar mensagem",
+	"pressToSend": "Pressione {{keyCombination}} para enviar",
 	"stopTts": "Parar conversão de texto em fala",
 	"typeMessage": "Digite uma mensagem...",
 	"typeTask": "Digite sua tarefa aqui...",
diff --git a/webview-ui/src/i18n/locales/pt-BR/settings.json b/webview-ui/src/i18n/locales/pt-BR/settings.json
index 8542cdd06649..942fc454d3fd 100644
--- a/webview-ui/src/i18n/locales/pt-BR/settings.json
+++ b/webview-ui/src/i18n/locales/pt-BR/settings.json
@@ -902,6 +902,10 @@
 		"collapseThinking": {
 			"label": "Recolher mensagens de pensamento por padrão",
 			"description": "Quando ativado, os blocos de pensamento serão recolhidos por padrão até que você interaja com eles"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Requer {primaryMod}+Enter para enviar mensagens",
+			"description": "Quando ativado, você deve pressionar {primaryMod}+Enter para enviar mensagens em vez de apenas Enter."
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/ru/chat.json b/webview-ui/src/i18n/locales/ru/chat.json
index 10cca124d355..22bfbc4a7d03 100644
--- a/webview-ui/src/i18n/locales/ru/chat.json
+++ b/webview-ui/src/i18n/locales/ru/chat.json
@@ -119,6 +119,7 @@
 	},
 	"addImages": "Добавить изображения к сообщению",
 	"sendMessage": "Отправить сообщение",
+	"pressToSend": "Нажмите {{keyCombination}}, чтобы отправить",
 	"stopTts": "Остановить синтез речи",
 	"typeMessage": "Введите сообщение...",
 	"typeTask": "Введите вашу задачу здесь...",
diff --git a/webview-ui/src/i18n/locales/ru/settings.json b/webview-ui/src/i18n/locales/ru/settings.json
index 5024290cf2e1..5f6e176ce629 100644
--- a/webview-ui/src/i18n/locales/ru/settings.json
+++ b/webview-ui/src/i18n/locales/ru/settings.json
@@ -902,6 +902,10 @@
 		"collapseThinking": {
 			"label": "Сворачивать сообщения о размышлениях по умолчанию",
 			"description": "Если включено, блоки с размышлениями будут свернуты по умолчанию, пока вы не начнете с ними взаимодействовать"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Требуется {primaryMod}+Enter для отправки сообщений",
+			"description": "Если включено, необходимо нажимать {primaryMod}+Enter для отправки сообщений вместо одной клавиши Enter."
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/tr/chat.json b/webview-ui/src/i18n/locales/tr/chat.json
index 9b92b937a799..6d34bab85fae 100644
--- a/webview-ui/src/i18n/locales/tr/chat.json
+++ b/webview-ui/src/i18n/locales/tr/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "Ek bağlamla istemi geliştir",
 	"addImages": "Mesaja resim ekle",
 	"sendMessage": "Mesaj gönder",
+	"pressToSend": "Göndermek için {{keyCombination}} tuşuna basın",
 	"stopTts": "Metin okumayı durdur",
 	"typeMessage": "Bir mesaj yazın...",
 	"typeTask": "Görevinizi buraya yazın...",
diff --git a/webview-ui/src/i18n/locales/tr/settings.json b/webview-ui/src/i18n/locales/tr/settings.json
index 338d52f19560..6165e35523d3 100644
--- a/webview-ui/src/i18n/locales/tr/settings.json
+++ b/webview-ui/src/i18n/locales/tr/settings.json
@@ -902,6 +902,10 @@
 		"collapseThinking": {
 			"label": "Düşünme mesajlarını varsayılan olarak daralt",
 			"description": "Etkinleştirildiğinde, düşünme blokları siz onlarla etkileşime girene kadar varsayılan olarak daraltılır"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Mesaj göndermek için {primaryMod}+Enter gerektirir",
+			"description": "Etkinleştirildiğinde, sadece Enter yerine mesaj göndermek için {primaryMod}+Enter tuşuna basmanız gerekir."
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/vi/chat.json b/webview-ui/src/i18n/locales/vi/chat.json
index 39cb1cf01663..a05b19d1cc45 100644
--- a/webview-ui/src/i18n/locales/vi/chat.json
+++ b/webview-ui/src/i18n/locales/vi/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "Nâng cao yêu cầu với ngữ cảnh bổ sung",
 	"addImages": "Thêm hình ảnh vào tin nhắn",
 	"sendMessage": "Gửi tin nhắn",
+	"pressToSend": "Nhấn {{keyCombination}} để gửi",
 	"stopTts": "Dừng chuyển văn bản thành giọng nói",
 	"typeMessage": "Nhập tin nhắn...",
 	"typeTask": "Nhập nhiệm vụ của bạn tại đây...",
diff --git a/webview-ui/src/i18n/locales/vi/settings.json b/webview-ui/src/i18n/locales/vi/settings.json
index 3df608458b15..124e874481a3 100644
--- a/webview-ui/src/i18n/locales/vi/settings.json
+++ b/webview-ui/src/i18n/locales/vi/settings.json
@@ -902,6 +902,10 @@
 		"collapseThinking": {
 			"label": "Thu gọn tin nhắn Suy nghĩ theo mặc định",
 			"description": "Khi được bật, các khối suy nghĩ sẽ được thu gọn theo mặc định cho đến khi bạn tương tác với chúng"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "Yêu cầu {primaryMod}+Enter để gửi tin nhắn",
+			"description": "Khi bật, bạn phải nhấn {primaryMod}+Enter để gửi tin nhắn thay vì chỉ nhấn Enter."
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/zh-CN/chat.json b/webview-ui/src/i18n/locales/zh-CN/chat.json
index ef87b819ea99..e619871d23ce 100644
--- a/webview-ui/src/i18n/locales/zh-CN/chat.json
+++ b/webview-ui/src/i18n/locales/zh-CN/chat.json
@@ -110,6 +110,7 @@
 	"enhancePrompt": "增强提示词",
 	"addImages": "添加图片到消息",
 	"sendMessage": "发送消息",
+	"pressToSend": "按 {{keyCombination}} 发送",
 	"stopTts": "停止文本转语音",
 	"typeMessage": "输入消息...",
 	"typeTask": "在此处输入您的任务...",
diff --git a/webview-ui/src/i18n/locales/zh-CN/settings.json b/webview-ui/src/i18n/locales/zh-CN/settings.json
index a1afc6f5963e..15a15aacdfe9 100644
--- a/webview-ui/src/i18n/locales/zh-CN/settings.json
+++ b/webview-ui/src/i18n/locales/zh-CN/settings.json
@@ -902,6 +902,10 @@
 		"collapseThinking": {
 			"label": "默认折叠“思考”消息",
 			"description": "启用后，“思考”块将默认折叠，直到您与其交互"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "发送消息需按 {primaryMod}+Enter",
+			"description": "启用时，你需要按 {primaryMod}+Enter 才能发送消息，而不是仅按 Enter。"
 		}
 	}
 }
diff --git a/webview-ui/src/i18n/locales/zh-TW/chat.json b/webview-ui/src/i18n/locales/zh-TW/chat.json
index 985859bec418..86a57efcde64 100644
--- a/webview-ui/src/i18n/locales/zh-TW/chat.json
+++ b/webview-ui/src/i18n/locales/zh-TW/chat.json
@@ -130,6 +130,7 @@
 	"enhancePromptDescription": "「強化提示詞」按鈕可透過提供額外內容、說明或改寫來協助改善您的提示詞。請試著在這裡輸入提示詞，然後再次點選按鈕，以了解其運作方式。",
 	"addImages": "新增圖片到訊息中",
 	"sendMessage": "傳送訊息",
+	"pressToSend": "按 {{keyCombination}} 發送",
 	"stopTts": "停止文字轉語音",
 	"typeMessage": "輸入訊息...",
 	"typeTask": "在這裡輸入您的工作...",
diff --git a/webview-ui/src/i18n/locales/zh-TW/settings.json b/webview-ui/src/i18n/locales/zh-TW/settings.json
index abc31b6bb355..53372c7411cc 100644
--- a/webview-ui/src/i18n/locales/zh-TW/settings.json
+++ b/webview-ui/src/i18n/locales/zh-TW/settings.json
@@ -902,6 +902,10 @@
 		"collapseThinking": {
 			"label": "預設折疊“思考”訊息",
 			"description": "啟用後，“思考”塊將預設折疊，直到您與其互動"
+		},
+		"requireCtrlEnterToSend": {
+			"label": "發送訊息需按 {primaryMod}+Enter",
+			"description": "啟用時，你需要按 {primaryMod}+Enter 才能發送訊息，而不是僅按 Enter。"
 		}
 	}
 }
diff --git a/webview-ui/src/utils/platform.ts b/webview-ui/src/utils/platform.ts
new file mode 100644
index 000000000000..0914f30aa905
--- /dev/null
+++ b/webview-ui/src/utils/platform.ts
@@ -0,0 +1,47 @@
+/**
+ * Platform detection utilities
+ */
+
+/**
+ * Detects if the current platform is macOS
+ * @returns boolean indicating if the platform is macOS
+ */
+export const isMacOS = (): boolean => {
+	// Check for macOS user agent or navigator platform
+	if (typeof navigator !== "undefined") {
+		return /Mac|iPod|iPhone|iPad/.test(navigator.platform)
+	}
+	return false
+}
+
+/**
+ * Gets the primary modifier key for the current platform
+ * @returns "Cmd" for macOS, "Ctrl" for other platforms
+ */
+export const getPrimaryModifierKey = (): string => {
+	return isMacOS() ? "Cmd" : "Ctrl"
+}
+
+/**
+ * Gets the primary modifier key symbol for the current platform
+ * @returns "⌘" for macOS, "Ctrl" for other platforms
+ */
+export const getPrimaryModifierSymbol = (): string => {
+	return isMacOS() ? "⌘" : "Ctrl"
+}
+
+/**
+ * Gets the platform-aware key combination for sending messages
+ * @returns "Cmd+Enter" for macOS, "Ctrl+Enter" for other platforms
+ */
+export const getSendMessageKeyCombination = (): string => {
+	return `${getPrimaryModifierKey()}+Enter`
+}
+
+/**
+ * Gets the platform-aware key combination symbol for sending messages
+ * @returns "⌘⏎" for macOS, "Ctrl+Enter" for other platforms
+ */
+export const getSendMessageKeyCombinationSymbol = (): string => {
+	return isMacOS() ? "⌘⏎" : "Ctrl+Enter"
+}