diff --git a/src/integrations/DiagnosticsMonitor.ts b/src/integrations/DiagnosticsMonitor.ts
index 2e6cd1b..7c1ff34 100644
--- a/src/integrations/DiagnosticsMonitor.ts
+++ b/src/integrations/DiagnosticsMonitor.ts
@@ -58,10 +58,23 @@ class DiagnosticsMonitor {
 			return currentDiagnostics
 		}
 
-		return this.waitForUpdatedDiagnostics()
+		let timeout = 300
+
+		// if diagnostics contain existing errors (since the check above didn't trigger) then it's likely claude just did something that should have fixed the error, so we'll give a longer grace period for diagnostics to catch up
+		const hasErrorsOrWarnings = currentDiagnostics.some(([_, diagnostics]) =>
+			diagnostics.some(
+				(d) =>
+					d.severity === vscode.DiagnosticSeverity.Error || d.severity === vscode.DiagnosticSeverity.Warning
+			)
+		)
+		if (hasErrorsOrWarnings) {
+			timeout = 5_000
+		}
+
+		return this.waitForUpdatedDiagnostics(timeout)
 	}
 
-	private async waitForUpdatedDiagnostics(timeout: number = 300): Promise<FileDiagnostics> {
+	private async waitForUpdatedDiagnostics(timeout: number): Promise<FileDiagnostics> {
 		return new Promise((resolve, reject) => {
 			const timer = setTimeout(() => {
 				cleanup()