diff --git a/lldb/tools/lldb-dap/src-ts/lldb-dap-server.ts b/lldb/tools/lldb-dap/src-ts/lldb-dap-server.ts
index 774be50053a17..280a11d807f6a 100644
--- a/lldb/tools/lldb-dap/src-ts/lldb-dap-server.ts
+++ b/lldb/tools/lldb-dap/src-ts/lldb-dap-server.ts
@@ -167,9 +167,12 @@ Restarting the server will interrupt any existing debug sessions and start a new
     return [
       path,
       ...args,
-      ...Object.entries(env ?? {}).map(
-        (entry) => String(entry[0]) + "=" + String(entry[1]),
-      ),
+      ...Object.entries(env ?? {})
+        // Filter and sort to avoid restarting the server just because the
+        // order of env changed or the log path changed.
+        .filter((entry) => String(entry[0]) !== "LLDBDAP_LOG")
+        .sort()
+        .map((entry) => String(entry[0]) + "=" + String(entry[1])),
     ];
   }
 }
diff --git a/lldb/tools/lldb-dap/src-ts/logging.ts b/lldb/tools/lldb-dap/src-ts/logging.ts
index 3b1c3c37ce1ce..7f3bbef9b027f 100644
--- a/lldb/tools/lldb-dap/src-ts/logging.ts
+++ b/lldb/tools/lldb-dap/src-ts/logging.ts
@@ -44,7 +44,7 @@ export class LogFilePathProvider {
     const logFolder = this.logFolder || this.context.logUri.fsPath;
     switch(type) {
     case LogType.DEBUG_SESSION:
-        return path.join(logFolder, `lldb-dap-session-${formatDate(new Date())}.log`);
+        return path.join(logFolder, `lldb-dap-${formatDate(new Date())}-${vscode.env.sessionId.split("-")[0]}.log`);
         break;
     }
   }