diff --git a/Ghidra/Debug/Debugger-agent-gdb/src/main/java/agent/gdb/manager/impl/GdbManagerImpl.java b/Ghidra/Debug/Debugger-agent-gdb/src/main/java/agent/gdb/manager/impl/GdbManagerImpl.java
index a2b5ab6949..28c14cbb1e 100644
--- a/Ghidra/Debug/Debugger-agent-gdb/src/main/java/agent/gdb/manager/impl/GdbManagerImpl.java
+++ b/Ghidra/Debug/Debugger-agent-gdb/src/main/java/agent/gdb/manager/impl/GdbManagerImpl.java
@@ -15,7 +15,7 @@
  */
 package agent.gdb.manager.impl;
 
-import static ghidra.async.AsyncUtils.loop;
+import static ghidra.async.AsyncUtils.*;
 
 import java.io.*;
 import java.util.*;
@@ -40,6 +40,7 @@ import ghidra.async.AsyncLock.Hold;
 import ghidra.dbg.error.DebuggerModelTerminatingException;
 import ghidra.dbg.util.HandlerMap;
 import ghidra.dbg.util.PrefixMap;
+import ghidra.framework.Application;
 import ghidra.lifecycle.Internal;
 import ghidra.util.Msg;
 import ghidra.util.datastruct.ListenerSet;
@@ -71,22 +72,9 @@ public class GdbManagerImpl implements GdbManager {
 		CLI, MI2;
 	}
 
-	private static final boolean LOG_IO = true |
-		Boolean.parseBoolean(System.getProperty("agent.gdb.manager.log"));
-	private static final PrintWriter DBG_LOG;
-	static {
-		if (LOG_IO) {
-			try {
-				DBG_LOG = new PrintWriter(new FileOutputStream(new File("GDB.log")));
-			}
-			catch (FileNotFoundException e) {
-				throw new AssertionError(e);
-			}
-		}
-		else {
-			DBG_LOG = null;
-		}
-	}
+	private static final boolean LOG_IO =
+		Boolean.getBoolean("agent.gdb.manager.log");
+	private static PrintWriter DBG_LOG = null;
 	private static final String PROMPT_GDB = "(gdb)";
 	public static final int INTERRUPT_MAX_RETRIES = 3;
 	public static final int INTERRUPT_RETRY_PERIOD_MILLIS = 100;
@@ -111,6 +99,9 @@ public class GdbManagerImpl implements GdbManager {
 
 		@Override
 		public void run() {
+			if (LOG_IO && DBG_LOG == null) {
+				initLog();
+			}
 			try {
 				String line;
 				while (isAlive() && null != (line = reader.readLine())) {
@@ -208,6 +199,20 @@ public class GdbManagerImpl implements GdbManager {
 		defaultHandlers();
 	}
 
+	private void initLog() {
+		try {
+			File userSettings = Application.getUserSettingsDirectory();
+			File logFile = new File(userSettings, "GDB.log");
+			if (!logFile.canWrite()) {
+				throw new AssertionError(logFile.getPath() + " appears to be unwritable");
+			}
+			DBG_LOG = new PrintWriter(new FileOutputStream(logFile));
+		}
+		catch (FileNotFoundException e) {
+			throw new AssertionError(e);
+		}
+	}
+
 	CompletableFuture<Void> event(Runnable r, String text) {
 		//Msg.debug(this, "Queueing event: " + text);
 		return CompletableFuture.runAsync(r, eventThread).exceptionally(ex -> {