diff --git a/src/common/components/context-menu.js b/src/common/components/context-menu.js
index 00999186..6b0bf59d 100644
--- a/src/common/components/context-menu.js
+++ b/src/common/components/context-menu.js
@@ -109,6 +109,8 @@ function ContextMenu({ params, onClose }) {
 	const [position, setPosition] = useState({ style: {} });
 	const [update, setUpdate] = useState();
 	const containerRef = useRef();
+	const searchStringRef = useRef('');
+	const searchTimeoutRef = useRef(null);
 
 	useEffect(() => {
 		setUpdate({});
@@ -147,6 +149,36 @@ function ContextMenu({ params, onClose }) {
 		}
 	}
 
+	function handleKeyDown(event) {
+		let { key } = event;
+		// Ignore non-characters
+		if (key.length !== 1 || !key.match(/\S/)) return;
+
+		// Clear search string after 3 seconds of no typing
+		if (searchTimeoutRef.current) {
+			clearTimeout(searchTimeoutRef.current);
+		}
+		searchTimeoutRef.current = setTimeout(() => {
+			searchStringRef.current = '';
+		}, 3000);
+
+		// Keep track of what has been typed so far
+		searchStringRef.current += key.toLowerCase();
+
+		// Find all buttons with text that start with what has been typed
+		let menuOptions = [...document.querySelectorAll(".context-menu button:not([disabled])")];
+		let candidates = menuOptions.filter(option => option.textContent.toLowerCase().startsWith(searchStringRef.current));
+		
+		// If there is only one candidate, click it right away
+		if (candidates.length == 1) {
+			candidates[0].click();
+		}
+		// If there are multiple - focus the first one
+		else if (candidates.length > 1) {
+			candidates[0].focus();
+		}
+	}
+
 	function handleClick(event, item) {
 		onClose();
 		event.preventDefault();
@@ -156,7 +188,7 @@ function ContextMenu({ params, onClose }) {
 
 	return (
 		<div className="context-menu-overlay" onPointerDown={handlePointerDown}>
-			<div ref={containerRef} className="context-menu" style={position.style}>
+			<div ref={containerRef} className="context-menu" style={position.style} data-tabstop={1} onKeyDown={handleKeyDown}>
 				{params.itemGroups.map((items, i) => (
 					<div key={i} className="group">
 						{items.map((item, i) => {
diff --git a/src/common/components/sidebar/annotations-view.js b/src/common/components/sidebar/annotations-view.js
index 9169abe6..34ec5271 100644
--- a/src/common/components/sidebar/annotations-view.js
+++ b/src/common/components/sidebar/annotations-view.js
@@ -175,7 +175,11 @@ const AnnotationsView = memo(React.forwardRef((props, ref) => {
 		props.onUpdateAnnotations([annotation]);
 	}, []);
 
-	function handlePointerDown() {
+	function handlePointerDown(event) {
+		// Clicking on the rendered content when a contextmenu is open will
+		// lead to pointerup event not firing and the annotation becoming not-selectable
+		// via keyboard until it is clicked.
+		if (event.target.classList.contains("context-menu-overlay")) return;
 		pointerDownRef.current = true;
 	}
 
diff --git a/src/common/keyboard-manager.js b/src/common/keyboard-manager.js
index 077fbd61..63dec15d 100644
--- a/src/common/keyboard-manager.js
+++ b/src/common/keyboard-manager.js
@@ -71,6 +71,11 @@ export class KeyboardManager {
 		// Escape must be pressed alone. We basically want to prevent
 		// Option-Escape (speak text on macOS) deselecting text
 		if (key === 'Escape') {
+			// If context menu is opened, close it and let focus return to last active element
+			if (document.querySelector(".context-menu")) {
+				this._reader.closeContextMenu();
+				return;
+			}
 			this._reader._lastView.focus();
 			this._reader.abortPrint();
 			this._reader._updateState({
diff --git a/src/common/reader.js b/src/common/reader.js
index 31ecc2fa..910fdc16 100644
--- a/src/common/reader.js
+++ b/src/common/reader.js
@@ -626,8 +626,7 @@ class Reader {
 		this._onBringReaderToFront?.(true);
 		this._updateState({ contextMenu: params });
 		setTimeout(() => {
-			window.focus();
-			document.activeElement.blur();
+			document.querySelector(".context-menu button:not([disabled])").focus();
 		});
 	}