diff --git a/extensions/typescript-language-features/src/typescriptServiceClient.ts b/extensions/typescript-language-features/src/typescriptServiceClient.ts
index 258fe3dccb7..ffcba61174e 100644
--- a/extensions/typescript-language-features/src/typescriptServiceClient.ts
+++ b/extensions/typescript-language-features/src/typescriptServiceClient.ts
@@ -652,14 +652,20 @@ export default class TypeScriptServiceClient extends Disposable implements IType
 				if (item === reportIssueItem) {
 					const minModernTsVersion = this.versionProvider.bundledVersion.apiVersion;
 
-					if (minModernTsVersion && this.apiVersion.lt(minModernTsVersion)) {
+					if (
+						minModernTsVersion &&
+						previousState.type === ServerState.Type.Errored &&
+						previousState.error instanceof TypeScriptServerError &&
+						previousState.error.version.apiVersion?.lt(minModernTsVersion)
+					) {
 						vscode.window.showWarningMessage(
 							vscode.l10n.t("Please update your TypeScript version"),
 							{
 								modal: true,
 								detail: vscode.l10n.t(
-									"The workspace is using an old version of TypeScript ({0}).\n\nBefore reporting an issue, please update the workspace to use the latest stable TypeScript release to make sure the bug has not already been fixed.",
-									(previousState.type === ServerState.Type.Errored && previousState.error instanceof TypeScriptServerError ? previousState.error.version.apiVersion?.displayName : undefined) + ''),
+									"The workspace is using an old version of TypeScript ({0}).\n\nBefore reporting an issue, please update the workspace to use TypeScript {1} or newer to make sure the bug has not already been fixed.",
+									previousState.error.version.apiVersion.displayName,
+									minModernTsVersion.displayName),
 							});
 					} else {
 						const args = previousState.type === ServerState.Type.Errored && previousState.error instanceof TypeScriptServerError