diff --git a/CHANGELOG.md b/CHANGELOG.md
index a0139a85d7bf..a55beb3f96f9 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -51,6 +51,8 @@ Docs: https://docs.openclaw.ai
 
 ### Fixes
 
+- **Dev-channel updates:** finish package-to-git switches in a fresh CLI process even when source SHA and version metadata are unchanged, preventing stale hashed chunks from loading after the global package root changes.
+- **Parallels release smoke:** preserve Windows installer reboot results across Parallels, wait for WSL MSI/default-version readiness, force explicit test-owned gateway stops, and reset Linux package, config, and cache state before install lanes, preventing false prerequisite, safety-gate, and stale-config failures.
 - **OpenAI Realtime Talk auth:** remove the non-public Codex OAuth realtime fallback and require an OpenAI Platform API key for Talk, Voice Call, and Discord realtime voice, preventing OAuth-only gateways from advertising a browser session that the live service rejects. Fixes #115021.
 - **Codex native controls:** stop misclassifying valid thinking/fast runtime controls as provider overrides so Codex routes keep their native controls, while provider-native objects and invalid values stay fail-closed. Thanks @VACInc. (#107588)
 - **State snapshot verification:** run SQLite snapshot verification in a separate process so worker-thread file closes no longer drop the Gateway's POSIX WAL locks, eliminating spurious WAL misses and I/O errors. Thanks @VACInc. (#114016)
diff --git a/scripts/e2e/parallels-windows-prepare.sh b/scripts/e2e/parallels-windows-prepare.sh
index 39addd825c7e..cb9399d17d2b 100755
--- a/scripts/e2e/parallels-windows-prepare.sh
+++ b/scripts/e2e/parallels-windows-prepare.sh
@@ -166,10 +166,31 @@ PY
 }
 
 run_windows_installer() {
+  local argv_base64
+  argv_base64="$(
+    python3 -c 'import base64, json, subprocess, sys; print(base64.b64encode(json.dumps({"executable": sys.argv[1], "argumentLine": subprocess.list2cmdline(sys.argv[2:])}).encode()).decode())' "$@"
+  )"
+  local guest_script
+  guest_script="
+    \$invocation = [Text.Encoding]::UTF8.GetString([Convert]::FromBase64String('${argv_base64}')) | ConvertFrom-Json
+    \$executable = [string]\$invocation.executable
+    \$process = Start-Process -FilePath \$executable -ArgumentList ([string]\$invocation.argumentLine) -NoNewWindow -Wait -PassThru
+    \$installerExitCode = \$process.ExitCode
+    switch (\$installerExitCode) {
+      0 { exit 0 }
+      1641 { exit 105 }
+      3010 { exit 194 }
+      default {
+        Write-Error ('Windows installer failed with exit code ' + \$installerExitCode + ': ' + \$executable)
+        exit 1
+      }
+    }
+  "
   local exit_code=0
-  run_bounded 1800 "$@" || exit_code=$?
-  # Windows success-with-reboot codes cross the POSIX boundary modulo 256.
-  # Accept 1641/3010 only for explicit DISM/installer calls; preserve all other failures.
+  run_bounded 1800 prlctl exec "$VM_NAME" powershell.exe \
+    -NoProfile -ExecutionPolicy Bypass -Command "$guest_script" || exit_code=$?
+  # Parallels collapses native Windows exit codes above 255 to 255. Normalize the two
+  # installer success-with-reboot codes in the guest so every other failure stays fatal.
   case "$exit_code" in
     0) return 0 ;;
     105) WINDOWS_REBOOT_STARTED=1; return 0 ;;
@@ -408,12 +429,12 @@ ensure_wsl_features() {
   local changed=0
   if [[ "$(feature_state Microsoft-Windows-Subsystem-Linux)" != "Enabled" ]]; then
     say "Enabling Microsoft-Windows-Subsystem-Linux"
-    run_windows_installer prlctl exec "$VM_NAME" dism.exe /online /enable-feature /featurename:Microsoft-Windows-Subsystem-Linux /all /norestart
+    run_windows_installer dism.exe /online /enable-feature /featurename:Microsoft-Windows-Subsystem-Linux /all /norestart
     changed=1
   fi
   if [[ "$(feature_state VirtualMachinePlatform)" != "Enabled" ]]; then
     say "Enabling VirtualMachinePlatform"
-    run_windows_installer prlctl exec "$VM_NAME" dism.exe /online /enable-feature /featurename:VirtualMachinePlatform /all /norestart
+    run_windows_installer dism.exe /online /enable-feature /featurename:VirtualMachinePlatform /all /norestart
     changed=1
   fi
   if [[ "$changed" == "1" ]]; then
@@ -438,9 +459,28 @@ raise SystemExit("No matching signed WSL MSI asset found")
 ' "$arch"
 }
 
+get_wsl_default_version() {
+  guest_user_ps "Get-ItemPropertyValue 'HKCU:/Software/Microsoft/Windows/CurrentVersion/Lxss' -Name DefaultVersion -ErrorAction SilentlyContinue" |
+    tr -d '\r' |
+    tail -n 1
+}
+
+ensure_wsl_default_version() {
+  local attempt
+  for attempt in $(seq 1 40); do
+    guest_user_cmd 'wsl.exe --set-default-version 2' >/dev/null 2>&1 || true
+    if [[ "$(get_wsl_default_version)" == "2" ]]; then
+      say "WSL default version ready"
+      return
+    fi
+    sleep 3
+  done
+  die "WSL default version did not become 2 within 120 seconds"
+}
+
 ensure_wsl_package() {
   if guest_user_cmd 'wsl.exe --version' >/dev/null 2>&1; then
-    guest_user_cmd 'wsl.exe --set-default-version 2' >/dev/null
+    ensure_wsl_default_version
     return
   fi
   local guest_arch asset_arch url signature wsl_msi
@@ -457,13 +497,12 @@ ensure_wsl_package() {
   run_bounded 720 prlctl exec "$VM_NAME" curl.exe -fL --connect-timeout 20 --max-time 600 "$url" -o "$wsl_msi" || die "WSL download transport exceeded 12 minutes"
   signature="$(guest_system_ps "\$signature = Get-AuthenticodeSignature '${wsl_msi}'; if (\$signature.Status -eq 'Valid' -and \$signature.SignerCertificate.Subject -match 'Microsoft Corporation') { 'Valid' } else { \$signature.Status.ToString() + ': ' + \$signature.SignerCertificate.Subject }" | tr -d '\r' | tail -n 1)"
   [[ "$signature" == "Valid" ]] || die "WSL MSI signature was not valid Microsoft code: $signature"
-  run_windows_installer prlctl exec "$VM_NAME" msiexec.exe /i 'C:\ProgramData\OpenClawPrerequisiteInstallers\WSL.msi' /qn /norestart '/L*v' 'C:\Windows\Temp\openclaw-wsl-install.log'
+  run_windows_installer msiexec.exe /i 'C:\ProgramData\OpenClawPrerequisiteInstallers\WSL.msi' /qn /norestart '/L*v' 'C:\Windows\Temp\openclaw-wsl-install.log'
   finish_installer_reboot
-  guest_user_cmd 'wsl.exe --version' >/dev/null || {
-    guest_system_ps "Get-Content 'C:/Windows/Temp/openclaw-wsl-install.log' -Tail 80" >&2 || true
-    die "WSL package install did not produce a working wsl.exe"
-  }
-  guest_user_cmd 'wsl.exe --set-default-version 2' >/dev/null
+  # Parallels can return from the MSI client before the Windows Installer service
+  # finishes publishing wsl.exe. Match the bounded readiness check used by Git and Node.
+  wait_for_check WSL 'wsl.exe --version'
+  ensure_wsl_default_version
   guest_system_ps "Remove-Item -LiteralPath '${wsl_msi}','C:/Windows/Temp/openclaw-wsl-install.log' -Force -ErrorAction SilentlyContinue"
 }
 
@@ -573,7 +612,7 @@ ensure_git() {
   [[ -n "$installer" ]] || die "winget did not download the Git installer"
   installer="$(stage_installer "$installer" Git 'Johannes Schindelin|Open Source Developer|Git for Windows' "$WINGET_EXPECTED_HASH")"
   say "Installing Git"
-  run_windows_installer prlctl exec "$VM_NAME" "$installer" /VERYSILENT /NORESTART /SP- /ALLUSERS
+  run_windows_installer "$installer" /VERYSILENT /NORESTART /SP- /ALLUSERS
   finish_installer_reboot
   wait_for_check Git 'where git.exe'
 }
@@ -588,7 +627,7 @@ ensure_node() {
   [[ -n "$installer" ]] || die "winget did not download the Node.js installer"
   installer="$(stage_installer "$installer" NodeJS 'OpenJS Foundation' "$WINGET_EXPECTED_HASH")"
   say "Installing Node.js LTS"
-  run_windows_installer prlctl exec "$VM_NAME" msiexec.exe /i "$installer" /qn /norestart
+  run_windows_installer msiexec.exe /i "$installer" /qn /norestart
   finish_installer_reboot
   wait_for_check Node.js 'where node.exe'
 }
@@ -605,7 +644,7 @@ verify_baseline() {
   guest_user_cmd 'wsl.exe --status' || die "WSL status failed"
   guest_system_ps "if (-not (Get-CimInstance Win32_ComputerSystem).HypervisorPresent) { throw 'Windows hypervisor is not active; WSL 2 workloads cannot start' }"
   local wsl_default
-  wsl_default="$(guest_user_ps "Get-ItemPropertyValue 'HKCU:/Software/Microsoft/Windows/CurrentVersion/Lxss' -Name DefaultVersion -ErrorAction SilentlyContinue" | tr -d '\r' | tail -n 1)"
+  wsl_default="$(get_wsl_default_version)"
   [[ "$wsl_default" == "2" ]] || die "WSL default version is ${wsl_default:-unset}, expected 2"
   assert_clean_product_state
   assert_no_pending_reboot
@@ -631,7 +670,7 @@ prepare() {
   ensure_node
   cleanup_installers
   restart_guest
-  guest_user_cmd 'wsl.exe --set-default-version 2' >/dev/null
+  ensure_wsl_default_version
   verify_baseline
   create_snapshot "$BASELINE_SNAPSHOT" "E2E-ready OpenClaw Windows baseline with WSL 2, Git, Node/npm, and no OpenClaw product state."
   say "Baseline ready: $BASELINE_SNAPSHOT"
diff --git a/scripts/e2e/parallels/linux-smoke.ts b/scripts/e2e/parallels/linux-smoke.ts
index ac94daf4a574..064ac1055167 100755
--- a/scripts/e2e/parallels/linux-smoke.ts
+++ b/scripts/e2e/parallels/linux-smoke.ts
@@ -333,6 +333,7 @@ class LinuxSmoke extends SmokeRunController<LinuxOptions> {
     await this.phase("fresh.bootstrap-guest", BOOTSTRAP_TIMEOUT_SECONDS, () =>
       this.bootstrapGuest(),
     );
+    await this.phase("fresh.reset-state", 180, () => this.resetState());
     await this.phase("fresh.preflight", 90, () => this.logGuestPreflight());
     await this.phase("fresh.install-latest-bootstrap", 420, () => this.installLatestRelease());
     await this.phase("fresh.install-main", 420, () =>
@@ -361,6 +362,7 @@ class LinuxSmoke extends SmokeRunController<LinuxOptions> {
     await this.phase("upgrade.bootstrap-guest", BOOTSTRAP_TIMEOUT_SECONDS, () =>
       this.bootstrapGuest(),
     );
+    await this.phase("upgrade.reset-state", 180, () => this.resetState());
     await this.phase("upgrade.preflight", 90, () => this.logGuestPreflight());
     await this.phase("upgrade.install-latest", 420, () => this.installLatestRelease());
     this.status.latestInstalledVersion = await this.extractLastVersion("upgrade.install-latest");
@@ -491,6 +493,16 @@ run_apt_with_lock_retry apt-get -o Acquire::Check-Date=false -o DPkg::Lock::Time
 run_apt_with_lock_retry apt-get -o DPkg::Lock::Timeout=30 install -y curl ca-certificates`);
   }
 
+  private resetState(): void {
+    this.guestBash(String.raw`set -euo pipefail
+pkill -f '[o]penclaw.*gateway run' >/dev/null 2>&1 || true
+pkill -f '[o]penclaw-gateway' >/dev/null 2>&1 || true
+pkill -f '[o]penclaw.mjs gateway' >/dev/null 2>&1 || true
+npm uninstall -g openclaw >/dev/null 2>&1 || true
+rm -rf /root/.openclaw /root/.npm/_cacache
+rm -f /tmp/openclaw-parallels-linux-gateway.log`);
+  }
+
   private installLatestRelease(): void {
     this.downloadGuestFile(this.options.installUrl, "/tmp/openclaw-install.sh");
     if (this.options.installVersion) {
diff --git a/scripts/e2e/parallels/windows-smoke.ts b/scripts/e2e/parallels/windows-smoke.ts
index 78b70daca933..6e29d6730a29 100755
--- a/scripts/e2e/parallels/windows-smoke.ts
+++ b/scripts/e2e/parallels/windows-smoke.ts
@@ -696,11 +696,12 @@ Invoke-OpenClaw update status --json`,
   }
 
   private gatewayAction(action: "restart" | "stop"): Promise<void> {
+    const forceFlag = action === "stop" ? " --force" : "";
     return this.guestPowerShellBackground(
       `gateway-${action}`,
       `$ErrorActionPreference = 'Continue'
 $PSNativeCommandUseErrorActionPreference = $false
-Invoke-OpenClaw gateway ${action}
+Invoke-OpenClaw gateway ${action}${forceFlag}
 if ($LASTEXITCODE -ne 0) { throw "gateway ${action} failed with exit code $LASTEXITCODE" }`,
       420_000,
     );
diff --git a/src/cli/update-cli/update-command-post-core.test.ts b/src/cli/update-cli/update-command-post-core.test.ts
index 139493f933ad..a216c080b613 100644
--- a/src/cli/update-cli/update-command-post-core.test.ts
+++ b/src/cli/update-cli/update-command-post-core.test.ts
@@ -3,7 +3,10 @@ import fs from "node:fs/promises";
 import os from "node:os";
 import path from "node:path";
 import { afterEach, describe, expect, it } from "vitest";
-import { readPostCorePluginInstallRecordsFile } from "./update-command-post-core.js";
+import {
+  readPostCorePluginInstallRecordsFile,
+  shouldResumePostCoreUpdateInFreshProcess,
+} from "./update-command-post-core.js";
 
 const tempDirs: string[] = [];
 
@@ -89,3 +92,45 @@ describe("readPostCorePluginInstallRecordsFile", () => {
     );
   });
 });
+
+describe("shouldResumePostCoreUpdateInFreshProcess", () => {
+  const unchangedGitResult = {
+    status: "ok" as const,
+    mode: "git" as const,
+    root: "/tmp/openclaw",
+    before: { sha: "abc123", version: "1.2.3" },
+    after: { sha: "abc123", version: "1.2.3" },
+    steps: [],
+    durationMs: 1,
+  };
+
+  it("uses the fresh CLI after an install-kind switch with unchanged git metadata", () => {
+    expect(
+      shouldResumePostCoreUpdateInFreshProcess({
+        result: unchangedGitResult,
+        downgradeRisk: false,
+        installKindChanged: true,
+      }),
+    ).toBe(true);
+  });
+
+  it("keeps a metadata-identical git update in process when the install kind is unchanged", () => {
+    expect(
+      shouldResumePostCoreUpdateInFreshProcess({
+        result: unchangedGitResult,
+        downgradeRisk: false,
+        installKindChanged: false,
+      }),
+    ).toBe(false);
+  });
+
+  it("does not resume after a failed install-kind switch", () => {
+    expect(
+      shouldResumePostCoreUpdateInFreshProcess({
+        result: { ...unchangedGitResult, status: "error" },
+        downgradeRisk: false,
+        installKindChanged: true,
+      }),
+    ).toBe(false);
+  });
+});
diff --git a/src/cli/update-cli/update-command-post-core.ts b/src/cli/update-cli/update-command-post-core.ts
index eb799ce17f59..7f65ba7217b9 100644
--- a/src/cli/update-cli/update-command-post-core.ts
+++ b/src/cli/update-cli/update-command-post-core.ts
@@ -636,8 +636,15 @@ export function didCoreUpdateChangeInstall(result: UpdateRunResult): boolean {
 export function shouldResumePostCoreUpdateInFreshProcess(params: {
   result: UpdateRunResult;
   downgradeRisk: boolean;
+  installKindChanged?: boolean;
 }): boolean {
-  return !params.downgradeRisk && didCoreUpdateChangeInstall(params.result);
+  // A package-to-git switch can land on the same version already cloned at its
+  // target SHA. The package root still changed, so old hashed chunks are unsafe.
+  return (
+    params.result.status === "ok" &&
+    !params.downgradeRisk &&
+    (params.installKindChanged === true || didCoreUpdateChangeInstall(params.result))
+  );
 }
 
 export async function writeControlPlaneUpdateRestartSentinelBestEffort(params: {
diff --git a/src/cli/update-cli/update-command-post-update.ts b/src/cli/update-cli/update-command-post-update.ts
index 733a58d0e16c..946920efb0ca 100644
--- a/src/cli/update-cli/update-command-post-update.ts
+++ b/src/cli/update-cli/update-command-post-update.ts
@@ -81,6 +81,7 @@ function pickUpdateQuip(): string {
 export async function finishUpdate(params: {
   result: UpdateRunResult;
   root: string;
+  installKindChanged: boolean;
   configSnapshot: Awaited<ReturnType<typeof readConfigFileSnapshot>>;
   requestedChannel: UpdateChannel | null;
   storedChannel: UpdateChannel | null;
@@ -161,6 +162,7 @@ export async function finishUpdate(params: {
   const shouldResumePostCoreInFreshProcess = shouldResumePostCoreUpdateInFreshProcess({
     result: params.result,
     downgradeRisk: params.downgradeRisk,
+    installKindChanged: params.installKindChanged,
   });
 
   let postUpdateConfigSnapshot: Awaited<ReturnType<typeof readConfigFileSnapshot>> | undefined;
diff --git a/src/cli/update-cli/update-command.ts b/src/cli/update-cli/update-command.ts
index 15c4a81fe4e2..d4c1a4e16306 100644
--- a/src/cli/update-cli/update-command.ts
+++ b/src/cli/update-cli/update-command.ts
@@ -573,6 +573,7 @@ async function updateCommandInternal(
   await finishUpdate({
     result,
     root,
+    installKindChanged: switchToGit || switchToPackage,
     configSnapshot,
     requestedChannel,
     storedChannel,
diff --git a/test/scripts/parallels-smoke-model.test.ts b/test/scripts/parallels-smoke-model.test.ts
index ba642184b160..6f9d83aaa38b 100644
--- a/test/scripts/parallels-smoke-model.test.ts
+++ b/test/scripts/parallels-smoke-model.test.ts
@@ -281,6 +281,13 @@ describe("Parallels smoke model selection", () => {
     expect(controller).toContain('prlctl stop "$VM_NAME" --acpi');
     expect(controller).toContain("HypervisorPresent");
     expect(controller).toContain("git --version && node --version && npm --version");
+    expect(controller).toContain("wait_for_check WSL 'wsl.exe --version'");
+    expect(controller).toContain("ensure_wsl_default_version");
+    expect(controller).toContain("WSL default version did not become 2 within 120 seconds");
+    expect(controller).toContain("1641 { exit 105 }");
+    expect(controller).toContain("3010 { exit 194 }");
+    expect(controller).toContain('run_bounded 1800 prlctl exec "$VM_NAME" powershell.exe');
+    expect(controller).not.toContain('run_windows_installer prlctl exec "$VM_NAME"');
     expect(controller).toContain(
       "if (Test-Path -LiteralPath '${GUEST_PROFILE_PS}/Downloads/OpenClawPrereqs')",
     );
@@ -289,6 +296,28 @@ describe("Parallels smoke model selection", () => {
     expect(controller).not.toContain("openclaw-windows-node");
   });
 
+  it("resets Linux product state before both install lanes", () => {
+    const linux = readFileSync(TS_PATHS.linux, "utf8");
+    for (const lane of ["fresh", "upgrade"]) {
+      const restoreIndex = linux.indexOf(`this.phase("${lane}.restore-snapshot"`);
+      const resetIndex = linux.indexOf(`this.phase("${lane}.reset-state"`);
+      const installIndex = linux.indexOf(
+        `this.phase("${lane}.${lane === "fresh" ? "install-latest-bootstrap" : "install-latest"}"`,
+      );
+      expect(restoreIndex).toBeGreaterThanOrEqual(0);
+      expect(resetIndex).toBeGreaterThan(restoreIndex);
+      expect(installIndex).toBeGreaterThan(resetIndex);
+    }
+    expect(linux).toContain("npm uninstall -g openclaw");
+    expect(linux).toContain("rm -rf /root/.openclaw /root/.npm/_cacache");
+  });
+
+  it("forces the explicit test-owned Windows gateway stop", () => {
+    const windows = readFileSync(TS_PATHS.windows, "utf8");
+    expect(windows).toContain('const forceFlag = action === "stop" ? " --force" : "";');
+    expect(windows).toContain("Invoke-OpenClaw gateway ${action}${forceFlag}");
+  });
+
   it("preserves caller arguments when loaded as the Windows controller library", () => {
     const result = spawnSync(
       "bash",