diff --git a/webview-ui/src/components/chat/ChatTextArea.tsx b/webview-ui/src/components/chat/ChatTextArea.tsx
index 6c541353eb..220e73e774 100644
--- a/webview-ui/src/components/chat/ChatTextArea.tsx
+++ b/webview-ui/src/components/chat/ChatTextArea.tsx
@@ -180,6 +180,7 @@ const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 		const contextMenuContainerRef = useRef<HTMLDivElement>(null)
 		const [isEnhancingPrompt, setIsEnhancingPrompt] = useState(false)
 		const [isFocused, setIsFocused] = useState(false)
+		const [screenReaderAnnouncement, setScreenReaderAnnouncement] = useState("")
 
 		// Use custom hook for prompt history navigation
 		const { handleHistoryNavigation, resetHistoryNavigation, resetOnInputChange } = usePromptHistory({
@@ -500,8 +501,16 @@ const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 				setCursorPosition(newCursorPosition)
 
 				const showMenu = shouldShowContextMenu(newValue, newCursorPosition)
+				const wasMenuVisible = showContextMenu
 				setShowContextMenu(showMenu)
 
+				// Announce menu state changes for screen readers
+				if (showMenu && !wasMenuVisible) {
+					setScreenReaderAnnouncement("File insertion menu opened")
+				} else if (!showMenu && wasMenuVisible) {
+					setScreenReaderAnnouncement("File insertion menu closed")
+				}
+
 				if (showMenu) {
 					if (newValue.startsWith("/")) {
 						// Handle slash command.
@@ -559,6 +568,48 @@ const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 			}
 		}, [showContextMenu])
 
+		// Announce selected menu item for screen readers
+		useEffect(() => {
+			if (showContextMenu && selectedMenuIndex >= 0) {
+				const options = getContextMenuOptions(
+					searchQuery,
+					inputValue,
+					selectedType,
+					queryItems,
+					fileSearchResults,
+					allModes,
+				)
+				const selectedOption = options[selectedMenuIndex]
+				if (selectedOption && selectedOption.type !== ContextMenuOptionType.NoResults) {
+					let announcement = ""
+					switch (selectedOption.type) {
+						case ContextMenuOptionType.File:
+						case ContextMenuOptionType.OpenedFile:
+							announcement = `File: ${selectedOption.value || selectedOption.label}, ${selectedMenuIndex + 1} of ${options.length}`
+							break
+						case ContextMenuOptionType.Folder:
+							announcement = `Folder: ${selectedOption.value || selectedOption.label}, ${selectedMenuIndex + 1} of ${options.length}`
+							break
+						case ContextMenuOptionType.Problems:
+							announcement = `Problems, ${selectedMenuIndex + 1} of ${options.length}`
+							break
+						case ContextMenuOptionType.Terminal:
+							announcement = `Terminal, ${selectedMenuIndex + 1} of ${options.length}`
+							break
+						case ContextMenuOptionType.Git:
+							announcement = `Git: ${selectedOption.label || selectedOption.value}, ${selectedMenuIndex + 1} of ${options.length}`
+							break
+						case ContextMenuOptionType.Mode:
+							announcement = `Mode: ${selectedOption.label}, ${selectedMenuIndex + 1} of ${options.length}`
+							break
+						default:
+							announcement = `${selectedOption.label || selectedOption.value}, ${selectedMenuIndex + 1} of ${options.length}`
+					}
+					setScreenReaderAnnouncement(announcement)
+				}
+			}
+		}, [showContextMenu, selectedMenuIndex, searchQuery, inputValue, selectedType, queryItems, fileSearchResults, allModes])
+
 		const handleBlur = useCallback(() => {
 			// Only hide the context menu if the user didn't click on it.
 			if (!isMouseDownOnMenu) {
@@ -1076,6 +1127,10 @@ const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 					minRows={3}
 					maxRows={15}
 					autoFocus={true}
+					aria-expanded={showContextMenu}
+					aria-haspopup="listbox"
+					aria-controls={showContextMenu ? "context-menu" : undefined}
+					aria-describedby="context-menu-instructions"
 					className={cn(
 						"w-full",
 						"text-vscode-input-foreground",
@@ -1249,6 +1304,26 @@ const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 							</div>
 						)}
 
+						{/* Live region for screen reader announcements */}
+						<div
+							aria-live="polite"
+							aria-atomic="true"
+							className="sr-only"
+							style={{
+								position: "absolute",
+								left: "-10000px",
+								width: "1px",
+								height: "1px",
+								overflow: "hidden",
+							}}>
+							{screenReaderAnnouncement}
+						</div>
+
+						{/* Instructions for screen readers */}
+						<div id="context-menu-instructions" className="sr-only">
+							Type @ to open file insertion menu. Use arrow keys to navigate, Enter to select, Escape to close.
+						</div>
+
 						{renderTextAreaSection()}
 					</div>
 
diff --git a/webview-ui/src/components/chat/ContextMenu.tsx b/webview-ui/src/components/chat/ContextMenu.tsx
index 1672c35ee3..55d13703ef 100644
--- a/webview-ui/src/components/chat/ContextMenu.tsx
+++ b/webview-ui/src/components/chat/ContextMenu.tsx
@@ -208,7 +208,11 @@ const ContextMenu: React.FC<ContextMenuProps> = ({
 			}}
 			onMouseDown={onMouseDown}>
 			<div
+				id="context-menu"
 				ref={menuRef}
+				role="listbox"
+				aria-label="File insertion menu"
+				aria-activedescendant={selectedIndex >= 0 ? `context-menu-option-${selectedIndex}` : undefined}
 				style={{
 					backgroundColor: "var(--vscode-dropdown-background)",
 					border: "1px solid var(--vscode-editorGroup-border)",
@@ -224,6 +228,10 @@ const ContextMenu: React.FC<ContextMenuProps> = ({
 					filteredOptions.map((option, index) => (
 						<div
 							key={`${option.type}-${option.value || index}`}
+							id={`context-menu-option-${index}`}
+							role="option"
+							aria-selected={index === selectedIndex && isOptionSelectable(option)}
+							aria-disabled={!isOptionSelectable(option)}
 							onClick={() => isOptionSelectable(option) && onSelect(option.type, option.value)}
 							style={{
 								padding: "4px 6px",