diff --git a/Core/WebServer.cpp b/Core/WebServer.cpp
index 1b4df8f1ee..7c30f989d2 100644
--- a/Core/WebServer.cpp
+++ b/Core/WebServer.cpp
@@ -854,9 +854,10 @@ static void WebServerThread() {
 		}
 	}
 
+	// Before RUNNING, so WebServerWaitForStartup() callers can read the port.
+	g_Config.iRemoteISOPort = http->Port();
 	UpdateStatus(ServerStatus::RUNNING);
 
-	g_Config.iRemoteISOPort = http->Port();
 	RegisterServer(http->Port());
 	double lastRegister = time_now_d();
 
diff --git a/Tools/wsdbg/src/main.rs b/Tools/wsdbg/src/main.rs
index 8730b7f1dc..daaa1c241c 100644
--- a/Tools/wsdbg/src/main.rs
+++ b/Tools/wsdbg/src/main.rs
@@ -294,10 +294,10 @@ fn launch_ppsspp(cmd: &[String]) -> Result<(std::process::Child, u16)> {
             child.kill().ok();
             child.wait().ok();
             Err(anyhow!(
-                "PPSSPP never reported a debugger port. It logs that line at NOTICE, so it should \
-                 survive any --loglevel - but a build predating that change logs it at INFO, where \
-                 --loglevel=3 hides it. Check the forwarded output above for 'Listening on port'; \
-                 if it isn't there, either raise --loglevel or pass an explicit --debugger=PORT."
+                "PPSSPP never reported a debugger port. Headless prints 'Debugger listening on port N' \
+                 to stderr whenever --debugger=0, with or without --log; other builds (and older \
+                 headless builds) only log it, so they need --log. Check the forwarded output above, \
+                 or pass an explicit --debugger=PORT."
             ))
         }
     }
diff --git a/headless/Headless.cpp b/headless/Headless.cpp
index b7adf0eb9e..06c6177dc4 100644
--- a/headless/Headless.cpp
+++ b/headless/Headless.cpp
@@ -1170,6 +1170,12 @@ int main(int argc, const char* argv[]) {
 			ShutdownWebServer();
 			return 1;
 		}
+		// With port 0 the OS picks one, and a client (wsdbg --launch) can only learn it from our
+		// output. Print it outside the log system so it doesn't depend on --log.
+		if (cmdLineOptions.DebuggerPort().value() == 0) {
+			fprintf(stderr, "Debugger listening on port %d\n", WebServerPort());
+			fflush(stderr);
+		}
 	}
 
 	if (cmdLineOptions.stateToSave.has_value()) {