diff --git a/extensions/markdown-language-features/src/languageFeatures/diagnostics.ts b/extensions/markdown-language-features/src/languageFeatures/diagnostics.ts
index fc0ea7989e4..44f79742a48 100644
--- a/extensions/markdown-language-features/src/languageFeatures/diagnostics.ts
+++ b/extensions/markdown-language-features/src/languageFeatures/diagnostics.ts
@@ -324,12 +324,18 @@ export class DiagnosticManager extends Disposable {
 
 		this._register(workspaceContents.onDidCreateMarkdownDocument(doc => {
 			this.triggerDiagnostics(doc.uri);
+			// Links in other files may have become valid
+			this.triggerForReferencingFiles(doc.uri);
 		}));
 
 		this._register(workspaceContents.onDidChangeMarkdownDocument(doc => {
 			this.triggerDiagnostics(doc.uri);
 		}));
 
+		this._register(workspaceContents.onDidDeleteMarkdownDocument(uri => {
+			this.triggerForReferencingFiles(uri);
+		}));
+
 		this._register(vscode.workspace.onDidCloseTextDocument(({ uri }) => {
 			this.pendingDiagnostics.delete(uri);
 			this.inFlightDiagnostics.cancel(uri);
@@ -337,7 +343,6 @@ export class DiagnosticManager extends Disposable {
 			this.reporter.delete(uri);
 		}));
 
-
 		this._register(this.linkWatcher.onDidChangeLinkedToFile(changedDocuments => {
 			for (const resource of changedDocuments) {
 				const doc = vscode.workspace.textDocuments.find(doc => doc.uri.toString() === resource.toString());
@@ -347,22 +352,28 @@ export class DiagnosticManager extends Disposable {
 			}
 		}));
 
-		this.tableOfContentsWatcher = this._register(new MdTableOfContentsWatcher(workspaceContents, tocProvider, delay));
-		this._register(this.tableOfContentsWatcher.onTocChanged(async e => {
-			// When the toc of a document changes, revalidate every file that linked to it too
-			const triggered = new ResourceMap<void>();
-			for (const ref of await this.referencesProvider.getAllReferencesToFile(e.uri, noopToken)) {
-				const file = ref.location.uri;
-				if (!triggered.has(file)) {
-					this.triggerDiagnostics(file);
-					triggered.set(file);
-				}
-			}
+		this.tableOfContentsWatcher = this._register(new MdTableOfContentsWatcher(workspaceContents, tocProvider, delay / 2));
+		this._register(this.tableOfContentsWatcher.onTocChanged(e => {
+			return this.triggerForReferencingFiles(e.uri);
 		}));
 
 		this.ready = this.rebuild();
 	}
 
+	private triggerForReferencingFiles(uri: vscode.Uri): Promise<void> {
+		return this.reporter.addWorkItem(
+			(async () => {
+				const triggered = new ResourceMap<Promise<void>>();
+				for (const ref of await this.referencesProvider.getAllReferencesToFile(uri, noopToken)) {
+					const file = ref.location.uri;
+					if (!triggered.has(file)) {
+						triggered.set(file, this.triggerDiagnostics(file));
+					}
+				}
+				await Promise.all(triggered.values());
+			})());
+	}
+
 	public override dispose() {
 		super.dispose();
 		this.pendingDiagnostics.clear();
diff --git a/extensions/markdown-language-features/src/test/diagnostic.test.ts b/extensions/markdown-language-features/src/test/diagnostic.test.ts
index c438f4a7333..dfc6051be3e 100644
--- a/extensions/markdown-language-features/src/test/diagnostic.test.ts
+++ b/extensions/markdown-language-features/src/test/diagnostic.test.ts
@@ -40,7 +40,7 @@ async function getComputedDiagnostics(doc: InMemoryDocument, workspace: MdWorksp
 }
 
 function assertDiagnosticsEqual(actual: readonly vscode.Diagnostic[], expectedRanges: readonly vscode.Range[]) {
-	assert.strictEqual(actual.length, expectedRanges.length);
+	assert.strictEqual(actual.length, expectedRanges.length, "Diagnostic count equal");
 
 	for (let i = 0; i < actual.length; ++i) {
 		assertRangeEqual(actual[i].range, expectedRanges[i], `Range ${i} to be equal`);
@@ -449,7 +449,7 @@ suite('Markdown: Diagnostics manager', () => {
 			tocProvider,
 			nulLogger,
 			0);
-		_disposables.push(manager, referencesProvider);
+		_disposables.push(linkProvider, tocProvider, referencesProvider, manager);
 		return manager;
 	}
 
@@ -554,4 +554,40 @@ suite('Markdown: Diagnostics manager', () => {
 			new vscode.Range(2, 7, 2, 17),
 		]);
 	});
+
+	test('Should revalidate linked files when file is deleted/created', async () => {
+		const doc1Uri = workspacePath('doc1.md');
+		const doc1 = new InMemoryDocument(doc1Uri, joinLines(
+			`[text](/doc2.md)`,
+			`[text](/doc2.md#header)`,
+		));
+		const doc2Uri = workspacePath('doc2.md');
+		const doc2 = new InMemoryDocument(doc2Uri, joinLines(
+			`# Header`
+		));
+
+		const workspace = new InMemoryWorkspaceMarkdownDocuments([doc1, doc2]);
+		const reporter = new MemoryDiagnosticReporter();
+
+		const manager = createDiagnosticsManager(workspace, new MemoryDiagnosticConfiguration({}), reporter);
+		await manager.ready;
+
+		// Check initial state
+		await reporter.waitPendingWork();
+		assertDiagnosticsEqual(reporter.get(doc1Uri), []);
+
+		// Edit header
+		workspace.deleteDocument(doc2Uri);
+
+		await reporter.waitPendingWork();
+		assertDiagnosticsEqual(reporter.get(doc1Uri), [
+			new vscode.Range(0, 7, 0, 15),
+			new vscode.Range(1, 7, 1, 22),
+		]);
+
+		// Revert to original file
+		workspace.createDocument(doc2);
+		await reporter.waitPendingWork();
+		assertDiagnosticsEqual(reporter.get(doc1Uri), []);
+	});
 });
diff --git a/extensions/markdown-language-features/src/util/tableOfContentsWatcher.ts b/extensions/markdown-language-features/src/util/tableOfContentsWatcher.ts
index 2fa5dc52bb9..c4a3c767def 100644
--- a/extensions/markdown-language-features/src/util/tableOfContentsWatcher.ts
+++ b/extensions/markdown-language-features/src/util/tableOfContentsWatcher.ts
@@ -5,11 +5,11 @@
 
 import * as vscode from 'vscode';
 import { MdTableOfContentsProvider, TableOfContents } from '../tableOfContents';
+import { MdWorkspaceContents, SkinnyTextDocument } from '../workspaceContents';
 import { equals } from './arrays';
+import { Delayer } from './async';
 import { Disposable } from './dispose';
 import { ResourceMap } from './resourceMap';
-import { MdWorkspaceContents, SkinnyTextDocument } from '../workspaceContents';
-import { Delayer } from './async';
 
 /**
  * Check if the items in a table of contents have changed.