diff --git a/src/vs/workbench/contrib/comments/browser/commentsController.ts b/src/vs/workbench/contrib/comments/browser/commentsController.ts
index 636de0344f6a2..fddb689229c59 100644
--- a/src/vs/workbench/contrib/comments/browser/commentsController.ts
+++ b/src/vs/workbench/contrib/comments/browser/commentsController.ts
@@ -240,6 +240,21 @@ class CommentingRangeDecorator {
 		}
 	}
 
+	private areRangesIntersectingOrTouchingByLine(a: Range, b: Range) {
+		// Check if `a` is before `b`
+		if (a.endLineNumber < b.startLineNumber) {
+			return false;
+		}
+
+		// Check if `b` is before `a`
+		if (b.endLineNumber < a.startLineNumber) {
+			return false;
+		}
+
+		// These ranges must intersect
+		return true;
+	}
+
 	public getMatchedCommentAction(commentRange: Range | undefined): CommentRangeAction[] {
 		if (commentRange === undefined) {
 			const foundInfos = this._infos?.filter(info => info.commentingRanges.fileComments);
@@ -260,7 +275,7 @@ class CommentingRangeDecorator {
 		const foundHoverActions = new Map<string, { range: Range; action: CommentRangeAction }>();
 		for (const decoration of this.commentingRangeDecorations) {
 			const range = decoration.getActiveRange();
-			if (range && ((range.startLineNumber <= commentRange.startLineNumber) || (commentRange.endLineNumber <= range.endLineNumber))) {
+			if (range && this.areRangesIntersectingOrTouchingByLine(range, commentRange)) {
 				// We can have several commenting ranges that match from the same owner because of how
 				// the line hover and selection decoration is done.
 				// The ranges must be merged so that we can see if the new commentRange fits within them.
@@ -863,6 +878,9 @@ export class CommentController implements IEditorContribution {
 		const newCommentInfos = this._commentingRangeDecorator.getMatchedCommentAction(range);
 		if (!newCommentInfos.length || !this.editor?.hasModel()) {
 			this._addInProgress = false;
+			if (!newCommentInfos.length) {
+				throw new Error('There are no commenting ranges at the current position.');
+			}
 			return Promise.resolve();
 		}
 
diff --git a/src/vs/workbench/contrib/comments/browser/commentsEditorContribution.ts b/src/vs/workbench/contrib/comments/browser/commentsEditorContribution.ts
index 116782e436446..b12521cf40b53 100644
--- a/src/vs/workbench/contrib/comments/browser/commentsEditorContribution.ts
+++ b/src/vs/workbench/contrib/comments/browser/commentsEditorContribution.ts
@@ -19,6 +19,7 @@ import { MenuId, MenuRegistry } from 'vs/platform/actions/common/actions';
 import { EditorContextKeys } from 'vs/editor/common/editorContextKeys';
 import { ActiveCursorHasCommentingRange, CommentController, ID } from 'vs/workbench/contrib/comments/browser/commentsController';
 import { IRange, Range } from 'vs/editor/common/core/range';
+import { INotificationService } from 'vs/platform/notification/common/notification';
 
 export class NextCommentThreadAction extends EditorAction {
 	constructor() {
@@ -87,9 +88,9 @@ MenuRegistry.appendMenuItem(MenuId.CommandPalette, {
 });
 
 const ADD_COMMENT_COMMAND = 'workbench.action.addComment';
-CommandsRegistry.registerCommand({
+KeybindingsRegistry.registerCommandAndKeybindingRule({
 	id: ADD_COMMENT_COMMAND,
-	handler: (accessor, args?: { range: IRange; fileComment: boolean }) => {
+	handler: async (accessor, args?: { range: IRange; fileComment: boolean }) => {
 		const activeEditor = getActiveEditor(accessor);
 		if (!activeEditor) {
 			return Promise.resolve();
@@ -102,8 +103,15 @@ CommandsRegistry.registerCommand({
 
 		const position = args?.range ? new Range(args.range.startLineNumber, args.range.startLineNumber, args.range.endLineNumber, args.range.endColumn)
 			: (args?.fileComment ? undefined : activeEditor.getSelection());
-		return controller.addOrToggleCommentAtLine(position, undefined);
-	}
+		const notificationService = accessor.get(INotificationService);
+		try {
+			await controller.addOrToggleCommentAtLine(position, undefined);
+		} catch (e) {
+			notificationService.error(nls.localize('comments.addCommand.error', "The cursor must be within a commenting range to add a comment")); // TODO: Once we have commands to go to next commenting range they should be included as buttons in the error.
+		}
+	},
+	weight: KeybindingWeight.EditorContrib,
+	primary: KeyMod.CtrlCmd | KeyMod.Alt | KeyCode.KeyC,
 });
 
 MenuRegistry.appendMenuItem(MenuId.CommandPalette, {