diff --git a/packages/wrangler/src/dev/miniflare.ts b/packages/wrangler/src/dev/miniflare.ts
index 4e911161f7b17..3e8412c23942a 100644
--- a/packages/wrangler/src/dev/miniflare.ts
+++ b/packages/wrangler/src/dev/miniflare.ts
@@ -450,7 +450,8 @@ function handleRuntimeStdio(stdout: Readable, stderr: Readable) {
 					`Address already in use (${address}). Please check that you are not already running a server on this address or specify a different port with --port.`
 				);
 
-				return;
+				// even though we've intercepted the chunk and logged a better error to stderr
+				// fallthrough to log the original chunk to the debug log file for observability
 			}
 
 			// IGNORABLE:
diff --git a/packages/wrangler/src/utils/debug-log-file.ts b/packages/wrangler/src/utils/debug-log-file.ts
index ea95833974e9d..ba309c4f5ea04 100644
--- a/packages/wrangler/src/utils/debug-log-file.ts
+++ b/packages/wrangler/src/utils/debug-log-file.ts
@@ -35,7 +35,7 @@ async function ensureDirectoryExists(filepath: string) {
 	await mkdir(dirpath, { recursive: true });
 }
 
-export const debugLogFilepath = path.resolve(getDebugFilepath());
+export const debugLogFilepath = getDebugFilepath();
 const mutex = new Mutex();
 
 let hasLoggedLocation = false;
@@ -54,25 +54,27 @@ ${message}
 ---
 `;
 
+	if (!hasLoggedLocation) {
+		hasLoggedLocation = true;
+		const relativeFilepath = path.relative(process.cwd(), debugLogFilepath);
+		console.info(`🐛 Writing debug logs to "${relativeFilepath}"`);
+		onExit(() => {
+			console.info(`🐛 Debug logs were written to "${relativeFilepath}"`);
+		});
+	}
+
 	await mutex.runWith(async () => {
 		try {
 			await ensureDirectoryExists(debugLogFilepath);
 			await appendFile(debugLogFilepath, entry);
 		} catch (err) {
-			if (hasLoggedError) return;
-			hasLoggedError = true;
-			console.error(`Failed to write to debug log file`, err);
-			console.error(`Would have written:`, entry);
+			if (!hasLoggedError) {
+				hasLoggedError = true;
+				console.error(`Failed to write to debug log file`, err);
+				console.error(`Would have written:`, entry);
+			}
 		}
 	});
-
-	if (hasLoggedLocation) return;
-	hasLoggedLocation = true;
-	const relativeFilepath = path.relative(process.cwd(), debugLogFilepath);
-	console.info(`🐛 Writing debug logs to "${relativeFilepath}"`);
-	onExit(() => {
-		console.info(`🐛 Debug logs were written to "${relativeFilepath}"`);
-	});
 }
 
 /**