diff --git a/src/lib/actions/sandbox/connect.ts b/src/lib/actions/sandbox/connect.ts
index 3bb4e38c548..df40efa0f8f 100644
--- a/src/lib/actions/sandbox/connect.ts
+++ b/src/lib/actions/sandbox/connect.ts
@@ -128,7 +128,7 @@ function runSandboxConnectProbe(sandboxName: string): void {
     process.exit(1);
   }
   if (processCheck.wasRunning) {
-    ensureSandboxInferenceRouteOrExit(sandboxName, { quiet: false });
+    ensureSandboxInferenceRoute(sandboxName, { quiet: true });
     if (processCheck.forwardRecovered) {
       console.log(
         `  Probe complete: ${agentName} gateway is running in '${sandboxName}'; restored dashboard port forward.`,
@@ -139,11 +139,11 @@ function runSandboxConnectProbe(sandboxName: string): void {
     return;
   }
   if (processCheck.recovered) {
-    ensureSandboxInferenceRouteOrExit(sandboxName, { quiet: false });
+    ensureSandboxInferenceRoute(sandboxName, { quiet: true });
     console.log(`  Probe complete: recovered ${agentName} gateway in '${sandboxName}'.`);
     return;
   }
-  ensureSandboxInferenceRouteOrExit(sandboxName, { quiet: false });
+  ensureSandboxInferenceRoute(sandboxName, { quiet: true });
   console.error(
     `  Probe failed: ${agentName} gateway is not running in '${sandboxName}' and automatic recovery failed.`,
   );
diff --git a/src/lib/onboard.ts b/src/lib/onboard.ts
index f4584f1266a..86a51d3f138 100644
--- a/src/lib/onboard.ts
+++ b/src/lib/onboard.ts
@@ -17,9 +17,7 @@ const {
 }: typeof import("./onboard/branding") = require("./onboard/branding");
 const { cleanupTempDir }: typeof import("./onboard/temp-files") = require("./onboard/temp-files");
 const { stopStaleDashboardListenersForSandbox } = require("./onboard/stale-gateway-cleanup");
-const {
-  runBackgroundForwardStartWithDiagnostics,
-}: typeof import("./onboard/forward-start") = require("./onboard/forward-start");
+const { looksLikeForwardPortConflict, runBackgroundForwardStartWithPortReleaseRetries }: typeof import("./onboard/forward-start") = require("./onboard/forward-start");
 const {
   ensureOllamaLoopbackSystemdOverride,
 }: typeof import("./onboard/ollama-systemd") = require("./onboard/ollama-systemd");
@@ -9303,17 +9301,16 @@ function ensureDashboardForward(
   parsedUrl.port = String(actualPort);
   const actualTarget = getDashboardForwardTarget(parsedUrl.toString());
   runOpenshell(["forward", "stop", String(actualPort)], { ignoreError: true });
-  const { result: fwdResult, diagnostic: fwdDiagnostic } =
-    runBackgroundForwardStartWithDiagnostics((stdio, timeout) =>
+  const { result: fwdResult, diagnostic: fwdDiagnostic } = runBackgroundForwardStartWithPortReleaseRetries(
+    (stdio, timeout) =>
       runOpenshell(
         ["forward", "start", "--background", actualTarget, sandboxName],
         { ignoreError: true, suppressOutput: true, stdio, timeout },
       ),
-    );
+    () => { sleep(1); runOpenshell(["forward", "stop", String(actualPort)], { ignoreError: true }); },
+  );
   if (fwdResult && fwdResult.status !== 0) {
-    const looksLikePortConflict =
-      fwdDiagnostic === "" ||
-      /eaddrinuse|address already in use|port .* in use|bind: .*in use/i.test(fwdDiagnostic);
+    const looksLikePortConflict = looksLikeForwardPortConflict(fwdDiagnostic);
     if (rollbackSandboxOnFailure) {
       // The sandbox was just created, committed to actualPort via its
       // baked-in CHAT_UI_URL and NEMOCLAW_DASHBOARD_PORT env. Silently
diff --git a/src/lib/onboard/forward-start.ts b/src/lib/onboard/forward-start.ts
index 2146203b6c0..05e45e958ad 100644
--- a/src/lib/onboard/forward-start.ts
+++ b/src/lib/onboard/forward-start.ts
@@ -37,6 +37,10 @@ function readDiagnosticFile(filePath: string): string {
   }
 }
 
+export function looksLikeForwardPortConflict(diagnostic: string): boolean {
+  return /eaddrinuse|address already in use|port .* in use|bind: .*in use/i.test(diagnostic);
+}
+
 export function runBackgroundForwardStartWithDiagnostics(
   runForwardStart: BackgroundForwardStartRunner,
   timeoutMs = 30_000,
@@ -82,3 +86,20 @@ export function runBackgroundForwardStartWithDiagnostics(
     cleanupTempDir(forwardDiagPath, "nemoclaw-forward-start");
   }
 }
+
+export function runBackgroundForwardStartWithPortReleaseRetries(
+  runForwardStart: BackgroundForwardStartRunner,
+  beforeRetry: () => void,
+  maxRetries = 3,
+): { result: BackgroundForwardStartResult; diagnostic: string } {
+  let attempt = runBackgroundForwardStartWithDiagnostics(runForwardStart);
+  for (
+    let retries = 0;
+    attempt.result.status !== 0 && looksLikeForwardPortConflict(attempt.diagnostic) && retries < maxRetries;
+    retries++
+  ) {
+    beforeRetry();
+    attempt = runBackgroundForwardStartWithDiagnostics(runForwardStart);
+  }
+  return attempt;
+}
diff --git a/test/onboard.test.ts b/test/onboard.test.ts
index f8ce6b019a0..a7be88adf86 100644
--- a/test/onboard.test.ts
+++ b/test/onboard.test.ts
@@ -10315,9 +10315,9 @@ const { createSandbox } = require(${onboardPath});
     assert.match(source, /if \(fwdResult && fwdResult\.status !== 0\)/);
     assert.match(source, /if \(rollbackSandboxOnFailure\)/);
     assert.match(source, /const looksLikePortConflict =/);
-    assert.match(source, /eaddrinuse\|address already in use/i);
+    assert.match(source, /looksLikeForwardPortConflict/);
     assert.match(source, /suppressOutput: true/);
-    assert.match(source, /runBackgroundForwardStartWithDiagnostics/);
+    assert.match(source, /runBackgroundForwardStartWithPortReleaseRetries/);
     assert.doesNotMatch(
       source,
       /forward", "start", "--background"[\s\S]{0,260}stdio: \["ignore", "pipe", "pipe"\]/,
@@ -10329,6 +10329,8 @@ const { createSandbox } = require(${onboardPath});
     );
     assert.match(helperSource, /secureTempFile\("nemoclaw-forward-start", "\.out"\)/);
     assert.match(helperSource, /runForwardStart\(\["ignore", outFd, errFd\], timeoutMs\)/);
+    assert.match(helperSource, /eaddrinuse\|address already in use/i);
+    assert.match(helperSource, /maxRetries = 3/);
     assert.match(
       source,
       /runOpenshell\(\["sandbox", "delete", sandboxName\], \{ ignoreError: true \}\)/,