diff --git a/frontend/src/components/common/SettingsModal.vue b/frontend/src/components/common/SettingsModal.vue
index 84c6eb4..f487f4e 100644
--- a/frontend/src/components/common/SettingsModal.vue
+++ b/frontend/src/components/common/SettingsModal.vue
@@ -174,8 +174,7 @@
                 <div class="space-y-2 text-xs">
                   <div class="flex justify-between py-1.5 border-b border-[#30363d]">
                     <span class="text-[var(--wraith-text-secondary)]">Version</span>
-                    <span class="text-[var(--wraith-text-primary)]">0.1.0-dev</span>
-                    <!-- TODO: Fetch from Wails binding — AppService.GetVersion() -->
+                    <span class="text-[var(--wraith-text-primary)]">{{ currentVersion }}</span>
                   </div>
                   <div class="flex justify-between py-1.5 border-b border-[#30363d]">
                     <span class="text-[var(--wraith-text-secondary)]">License</span>
@@ -183,7 +182,7 @@
                   </div>
                   <div class="flex justify-between py-1.5 border-b border-[#30363d]">
                     <span class="text-[var(--wraith-text-secondary)]">Runtime</span>
-                    <span class="text-[var(--wraith-text-primary)]">Wails v2</span>
+                    <span class="text-[var(--wraith-text-primary)]">Wails v3</span>
                   </div>
                   <div class="flex justify-between py-1.5">
                     <span class="text-[var(--wraith-text-secondary)]">Frontend</span>
@@ -191,6 +190,47 @@
                   </div>
                 </div>
 
+                <!-- Check for Updates -->
+                <div class="pt-2">
+                  <button
+                    class="w-full px-3 py-2 text-xs rounded border transition-colors cursor-pointer flex items-center justify-center gap-2"
+                    :class="updateCheckState === 'found'
+                      ? 'border-[#3fb950] text-[#3fb950] hover:bg-[#3fb950]/10'
+                      : 'border-[#30363d] text-[var(--wraith-text-primary)] hover:bg-[#30363d]'"
+                    :disabled="updateCheckState === 'checking'"
+                    @click="checkForUpdates"
+                  >
+                    <template v-if="updateCheckState === 'idle'">
+                      <svg class="w-3.5 h-3.5" viewBox="0 0 16 16" fill="currentColor">
+                        <path d="M1.705 8.005a.75.75 0 0 1 .834.656 5.5 5.5 0 0 0 9.592 2.97l-1.204-1.204a.25.25 0 0 1 .177-.427h3.646a.25.25 0 0 1 .25.25v3.646a.25.25 0 0 1-.427.177l-1.38-1.38A7.002 7.002 0 0 1 1.05 8.84a.75.75 0 0 1 .656-.834ZM8 2.5a5.487 5.487 0 0 0-4.131 1.869l1.204 1.204A.25.25 0 0 1 4.896 6H1.25A.25.25 0 0 1 1 5.75V2.104a.25.25 0 0 1 .427-.177l1.38 1.38A7.002 7.002 0 0 1 14.95 7.16a.75.75 0 0 1-1.49.178A5.5 5.5 0 0 0 8 2.5Z" />
+                      </svg>
+                      Check for Updates
+                    </template>
+                    <template v-else-if="updateCheckState === 'checking'">
+                      <svg class="w-3.5 h-3.5 animate-spin" viewBox="0 0 16 16" fill="currentColor">
+                        <path d="M8 0a8 8 0 1 0 0 16A8 8 0 0 0 8 0ZM1.5 8a6.5 6.5 0 1 1 13 0 6.5 6.5 0 0 1-13 0Z" opacity=".25" />
+                        <path d="M8 0a8 8 0 0 1 8 8h-1.5A6.5 6.5 0 0 0 8 1.5V0Z" />
+                      </svg>
+                      Checking...
+                    </template>
+                    <template v-else-if="updateCheckState === 'found'">
+                      <svg class="w-3.5 h-3.5" viewBox="0 0 16 16" fill="currentColor">
+                        <path d="M8 2a6 6 0 1 0 0 12A6 6 0 0 0 8 2Zm.75 3.5v3.69l1.72-1.72a.75.75 0 1 1 1.06 1.06l-3 3a.75.75 0 0 1-1.06 0l-3-3a.75.75 0 1 1 1.06-1.06l1.72 1.72V5.5a.75.75 0 0 1 1.5 0Z" />
+                      </svg>
+                      v{{ latestVersion }} available — click to download
+                    </template>
+                    <template v-else-if="updateCheckState === 'up-to-date'">
+                      <svg class="w-3.5 h-3.5" viewBox="0 0 16 16" fill="currentColor">
+                        <path d="M13.78 4.22a.75.75 0 0 1 0 1.06l-7.25 7.25a.75.75 0 0 1-1.06 0L2.22 9.28a.751.751 0 0 1 .018-1.042.751.751 0 0 1 1.042-.018L6 10.94l6.72-6.72a.75.75 0 0 1 1.06 0Z" />
+                      </svg>
+                      You're up to date
+                    </template>
+                    <template v-else-if="updateCheckState === 'error'">
+                      Could not check for updates
+                    </template>
+                  </button>
+                </div>
+
                 <div class="flex gap-2 pt-2">
                   <a
                     href="#"
@@ -276,6 +316,12 @@ const settings = ref({
   scrollbackBuffer: 5000,
 });
 
+// --- Update check state ---
+type UpdateCheckState = "idle" | "checking" | "found" | "up-to-date" | "error";
+const updateCheckState = ref<UpdateCheckState>("idle");
+const currentVersion = ref("0.1.0-dev");
+const latestVersion = ref("");
+
 function open(): void {
   visible.value = true;
   activeSection.value = "general";
@@ -301,6 +347,35 @@ function importVault(): void {
   alert("Import vault — not yet implemented (requires Wails binding)");
 }
 
+async function checkForUpdates(): Promise<void> {
+  if (updateCheckState.value === "checking") return;
+
+  if (updateCheckState.value === "found") {
+    // Second click — trigger download
+    // TODO: replace with Wails binding — UpdateService.DownloadUpdate() + ApplyUpdate()
+    console.log("Download update:", latestVersion.value);
+    return;
+  }
+
+  updateCheckState.value = "checking";
+  try {
+    // TODO: replace with Wails binding — UpdateService.CheckForUpdate()
+    // const info = await UpdateService.CheckForUpdate();
+    // currentVersion.value = info.currentVersion;
+    // if (info.available) {
+    //   latestVersion.value = info.latestVersion;
+    //   updateCheckState.value = "found";
+    // } else {
+    //   updateCheckState.value = "up-to-date";
+    // }
+
+    // Placeholder until Wails bindings are generated:
+    updateCheckState.value = "up-to-date";
+  } catch {
+    updateCheckState.value = "error";
+  }
+}
+
 function openLink(target: string): void {
   // TODO: Replace with Wails runtime.BrowserOpenURL(url)
   const urls: Record<string, string> = {
diff --git a/frontend/src/components/common/StatusBar.vue b/frontend/src/components/common/StatusBar.vue
index f962b3c..d2bb9d4 100644
--- a/frontend/src/components/common/StatusBar.vue
+++ b/frontend/src/components/common/StatusBar.vue
@@ -18,8 +18,33 @@
       </template>
     </div>
 
-    <!-- Right: terminal info -->
+    <!-- Right: terminal info + update notification -->
     <div class="flex items-center gap-3">
+      <!-- Update notification pill -->
+      <button
+        v-if="updateAvailable && updateInfo"
+        class="flex items-center gap-1.5 px-2 py-0.5 rounded-full text-[10px] font-medium transition-colors cursor-pointer"
+        :class="updateState === 'downloading'
+          ? 'bg-[#1f6feb]/30 text-[#58a6ff]'
+          : 'bg-[#1f6feb]/20 text-[#58a6ff] hover:bg-[#1f6feb]/30'"
+        :disabled="updateState === 'downloading'"
+        @click="handleUpdate"
+      >
+        <template v-if="updateState === 'idle'">
+          <svg class="w-3 h-3" viewBox="0 0 16 16" fill="currentColor">
+            <path d="M8 2a6 6 0 1 0 0 12A6 6 0 0 0 8 2Zm.75 3.5v3.69l1.72-1.72a.75.75 0 1 1 1.06 1.06l-3 3a.75.75 0 0 1-1.06 0l-3-3a.75.75 0 1 1 1.06-1.06l1.72 1.72V5.5a.75.75 0 0 1 1.5 0Z" />
+          </svg>
+          v{{ updateInfo.latestVersion }} available &mdash; Update
+        </template>
+        <template v-else-if="updateState === 'downloading'">
+          <svg class="w-3 h-3 animate-spin" viewBox="0 0 16 16" fill="currentColor">
+            <path d="M8 0a8 8 0 1 0 0 16A8 8 0 0 0 8 0ZM1.5 8a6.5 6.5 0 1 1 13 0 6.5 6.5 0 0 1-13 0Z" opacity=".25" />
+            <path d="M8 0a8 8 0 0 1 8 8h-1.5A6.5 6.5 0 0 0 8 1.5V0Z" />
+          </svg>
+          Downloading...
+        </template>
+      </button>
+
       <button
         class="hover:text-[var(--wraith-text-primary)] transition-colors cursor-pointer"
         title="Change terminal theme"
@@ -34,7 +59,7 @@
 </template>
 
 <script setup lang="ts">
-import { computed, ref } from "vue";
+import { computed, ref, onMounted } from "vue";
 import { useSessionStore } from "@/stores/session.store";
 import { useConnectionStore } from "@/stores/connection.store";
 
@@ -47,6 +72,18 @@ const emit = defineEmits<{
   (e: "open-theme-picker"): void;
 }>();
 
+interface UpdateInfoData {
+  available: boolean;
+  currentVersion: string;
+  latestVersion: string;
+  downloadUrl: string;
+  sha256: string;
+}
+
+const updateAvailable = ref(false);
+const updateInfo = ref<UpdateInfoData | null>(null);
+const updateState = ref<"idle" | "downloading">("idle");
+
 const connectionInfo = computed(() => {
   const session = sessionStore.activeSession;
   if (!session) return "";
@@ -57,9 +94,38 @@ const connectionInfo = computed(() => {
   return `root@${conn.hostname}:${conn.port}`;
 });
 
+/** Check for updates on mount. */
+onMounted(async () => {
+  try {
+    // TODO: replace with Wails binding — UpdateService.CheckForUpdate()
+    // const info = await UpdateService.CheckForUpdate();
+    // if (info.available) {
+    //   updateAvailable.value = true;
+    //   updateInfo.value = info;
+    // }
+  } catch {
+    // Silent fail — update check is non-critical.
+  }
+});
+
+/** Download and apply an update. */
+async function handleUpdate(): Promise<void> {
+  if (!updateInfo.value || updateState.value === "downloading") return;
+  updateState.value = "downloading";
+  try {
+    // TODO: replace with Wails bindings
+    // const path = await UpdateService.DownloadUpdate(updateInfo.value);
+    // await UpdateService.ApplyUpdate(path);
+    console.log("Update download triggered for", updateInfo.value.latestVersion);
+  } catch (e) {
+    console.error("Update failed:", e);
+    updateState.value = "idle";
+  }
+}
+
 function setThemeName(name: string): void {
   activeThemeName.value = name;
 }
 
-defineExpose({ setThemeName, activeThemeName });
+defineExpose({ setThemeName, activeThemeName, updateAvailable, updateInfo });
 </script>
diff --git a/internal/app/app.go b/internal/app/app.go
index 329c8ef..6d0e0df 100644
--- a/internal/app/app.go
+++ b/internal/app/app.go
@@ -19,6 +19,7 @@ import (
 	"github.com/vstockwell/wraith/internal/sftp"
 	"github.com/vstockwell/wraith/internal/ssh"
 	"github.com/vstockwell/wraith/internal/theme"
+	"github.com/vstockwell/wraith/internal/updater"
 	"github.com/vstockwell/wraith/internal/vault"
 )
 
@@ -37,13 +38,16 @@ type WraithApp struct {
 	RDP         *rdp.RDPService
 	Credentials *credentials.CredentialService
 	AI          *ai.AIService
+	Updater     *updater.UpdateService
 	oauthMgr    *ai.OAuthManager
 	unlocked    bool
 }
 
 // New creates and initializes the WraithApp, opening the database, running
 // migrations, creating all services, and seeding built-in themes.
-func New() (*WraithApp, error) {
+// The version string is the build-time semver (e.g. "0.2.0") used by the
+// auto-updater to check for newer releases.
+func New(version string) (*WraithApp, error) {
 	dataDir := dataDirectory()
 	dbPath := filepath.Join(dataDir, "wraith.db")
 
@@ -95,6 +99,8 @@ func New() (*WraithApp, error) {
 		slog.Warn("failed to seed themes", "error", err)
 	}
 
+	updaterSvc := updater.NewUpdateService(version)
+
 	return &WraithApp{
 		db:          database,
 		Settings:    settingsSvc,
@@ -106,6 +112,7 @@ func New() (*WraithApp, error) {
 		SFTP:        sftpSvc,
 		RDP:         rdpSvc,
 		AI:          aiSvc,
+		Updater:     updaterSvc,
 		oauthMgr:    oauthMgr,
 	}, nil
 }
diff --git a/internal/updater/service.go b/internal/updater/service.go
new file mode 100644
index 0000000..49d61fe
--- /dev/null
+++ b/internal/updater/service.go
@@ -0,0 +1,292 @@
+package updater
+
+import (
+	"crypto/sha256"
+	"encoding/hex"
+	"encoding/json"
+	"fmt"
+	"io"
+	"log/slog"
+	"net/http"
+	"os"
+	"os/exec"
+	"path/filepath"
+	"runtime"
+	"strconv"
+	"strings"
+	"time"
+)
+
+// UpdateInfo describes the result of checking for an available update.
+type UpdateInfo struct {
+	Available   bool   `json:"available"`
+	CurrentVer  string `json:"currentVersion"`
+	LatestVer   string `json:"latestVersion"`
+	DownloadURL string `json:"downloadUrl"`
+	SHA256      string `json:"sha256"`
+}
+
+// UpdateService checks a Gitea generic-package registry for new versions
+// and can download + launch an installer to apply the update.
+type UpdateService struct {
+	currentVersion string
+	baseURL        string // e.g. https://git.command.vigilcyber.com
+	owner          string // e.g. vstockwell
+	pkg            string // e.g. wraith
+	httpClient     *http.Client
+}
+
+// NewUpdateService creates an UpdateService that compares against the
+// supplied currentVersion (semver without "v" prefix, e.g. "0.2.0").
+func NewUpdateService(currentVersion string) *UpdateService {
+	return &UpdateService{
+		currentVersion: strings.TrimPrefix(currentVersion, "v"),
+		baseURL:        "https://git.command.vigilcyber.com",
+		owner:          "vstockwell",
+		pkg:            "wraith",
+		httpClient: &http.Client{
+			Timeout: 30 * time.Second,
+		},
+	}
+}
+
+// giteaPackageVersion is the subset of the Gitea API response we need.
+type giteaPackageVersion struct {
+	Version string `json:"version"`
+}
+
+// versionJSON is the schema of the version.json file in the package.
+type versionJSON struct {
+	Version     string `json:"version"`
+	SHA256      string `json:"sha256"`
+	DownloadURL string `json:"downloadUrl"`
+}
+
+// CheckForUpdate queries the Gitea package API for the latest version and
+// compares it with the current version using semver comparison.
+func (u *UpdateService) CheckForUpdate() (*UpdateInfo, error) {
+	info := &UpdateInfo{
+		CurrentVer: u.currentVersion,
+	}
+
+	// Fetch latest package version from the Gitea API.
+	apiURL := fmt.Sprintf(
+		"%s/api/v1/packages/%s/generic/%s?limit=1&sort=created_at&direction=desc",
+		u.baseURL, u.owner, u.pkg,
+	)
+
+	slog.Info("checking for updates", "url", apiURL)
+
+	req, err := http.NewRequest("GET", apiURL, nil)
+	if err != nil {
+		return nil, fmt.Errorf("build request: %w", err)
+	}
+
+	// Use GIT_TOKEN for private registries, if available.
+	if token := os.Getenv("GIT_TOKEN"); token != "" {
+		req.Header.Set("Authorization", "token "+token)
+	}
+
+	resp, err := u.httpClient.Do(req)
+	if err != nil {
+		return nil, fmt.Errorf("fetch package versions: %w", err)
+	}
+	defer resp.Body.Close()
+
+	if resp.StatusCode != http.StatusOK {
+		return nil, fmt.Errorf("unexpected status %d from package API", resp.StatusCode)
+	}
+
+	var versions []giteaPackageVersion
+	if err := json.NewDecoder(resp.Body).Decode(&versions); err != nil {
+		return nil, fmt.Errorf("decode package versions: %w", err)
+	}
+
+	if len(versions) == 0 {
+		slog.Info("no package versions found")
+		return info, nil
+	}
+
+	latestVer := strings.TrimPrefix(versions[0].Version, "v")
+	info.LatestVer = latestVer
+
+	cmp := CompareVersions(u.currentVersion, latestVer)
+	if cmp >= 0 {
+		slog.Info("already up to date", "current", u.currentVersion, "latest", latestVer)
+		return info, nil
+	}
+
+	// Newer version is available — fetch version.json for SHA256 + download URL.
+	versionInfoURL := fmt.Sprintf(
+		"%s/api/packages/%s/generic/%s/%s/version.json",
+		u.baseURL, u.owner, u.pkg, versions[0].Version,
+	)
+
+	vInfo, err := u.fetchVersionJSON(versionInfoURL)
+	if err != nil {
+		// Non-fatal: we still know the version is available, just no SHA256.
+		slog.Warn("could not fetch version.json", "error", err)
+	}
+
+	info.Available = true
+
+	if vInfo != nil {
+		info.SHA256 = vInfo.SHA256
+		if vInfo.DownloadURL != "" {
+			info.DownloadURL = vInfo.DownloadURL
+		}
+	}
+
+	if info.DownloadURL == "" {
+		info.DownloadURL = fmt.Sprintf(
+			"%s/api/packages/%s/generic/%s/%s/wraith-%s-setup.exe",
+			u.baseURL, u.owner, u.pkg, versions[0].Version, versions[0].Version,
+		)
+	}
+
+	slog.Info("update available", "current", u.currentVersion, "latest", latestVer)
+	return info, nil
+}
+
+// fetchVersionJSON fetches and decodes a version.json file from the given URL.
+func (u *UpdateService) fetchVersionJSON(url string) (*versionJSON, error) {
+	req, err := http.NewRequest("GET", url, nil)
+	if err != nil {
+		return nil, err
+	}
+	if token := os.Getenv("GIT_TOKEN"); token != "" {
+		req.Header.Set("Authorization", "token "+token)
+	}
+
+	resp, err := u.httpClient.Do(req)
+	if err != nil {
+		return nil, err
+	}
+	defer resp.Body.Close()
+
+	if resp.StatusCode != http.StatusOK {
+		return nil, fmt.Errorf("status %d", resp.StatusCode)
+	}
+
+	var v versionJSON
+	if err := json.NewDecoder(resp.Body).Decode(&v); err != nil {
+		return nil, err
+	}
+	return &v, nil
+}
+
+// DownloadUpdate downloads the installer for the given version to a temporary
+// file and returns its path. If the UpdateInfo includes a SHA256 hash the
+// download is verified against it.
+func (u *UpdateService) DownloadUpdate(info *UpdateInfo) (string, error) {
+	if info.DownloadURL == "" {
+		return "", fmt.Errorf("no download URL")
+	}
+
+	slog.Info("downloading update", "url", info.DownloadURL)
+
+	req, err := http.NewRequest("GET", info.DownloadURL, nil)
+	if err != nil {
+		return "", fmt.Errorf("build request: %w", err)
+	}
+	if token := os.Getenv("GIT_TOKEN"); token != "" {
+		req.Header.Set("Authorization", "token "+token)
+	}
+
+	resp, err := u.httpClient.Do(req)
+	if err != nil {
+		return "", fmt.Errorf("download installer: %w", err)
+	}
+	defer resp.Body.Close()
+
+	if resp.StatusCode != http.StatusOK {
+		return "", fmt.Errorf("unexpected status %d downloading installer", resp.StatusCode)
+	}
+
+	// Write to a temp file.
+	tmpDir := os.TempDir()
+	filename := fmt.Sprintf("wraith-%s-setup.exe", info.LatestVer)
+	destPath := filepath.Join(tmpDir, filename)
+
+	f, err := os.Create(destPath)
+	if err != nil {
+		return "", fmt.Errorf("create temp file: %w", err)
+	}
+	defer f.Close()
+
+	hasher := sha256.New()
+	writer := io.MultiWriter(f, hasher)
+
+	if _, err := io.Copy(writer, resp.Body); err != nil {
+		os.Remove(destPath)
+		return "", fmt.Errorf("write installer: %w", err)
+	}
+
+	// Verify SHA256 if provided.
+	if info.SHA256 != "" {
+		got := hex.EncodeToString(hasher.Sum(nil))
+		if !strings.EqualFold(got, info.SHA256) {
+			os.Remove(destPath)
+			return "", fmt.Errorf("SHA256 mismatch: expected %s, got %s", info.SHA256, got)
+		}
+		slog.Info("SHA256 verified", "hash", got)
+	}
+
+	slog.Info("update downloaded", "path", destPath)
+	return destPath, nil
+}
+
+// ApplyUpdate launches the downloaded installer and signals the caller to
+// exit. On Windows it starts the exe; on other platforms it logs a message.
+func (u *UpdateService) ApplyUpdate(installerPath string) error {
+	slog.Info("applying update", "installer", installerPath)
+
+	if runtime.GOOS == "windows" {
+		cmd := exec.Command(installerPath, "/SILENT")
+		if err := cmd.Start(); err != nil {
+			return fmt.Errorf("launch installer: %w", err)
+		}
+		// The caller (frontend) should exit the app after this returns.
+		return nil
+	}
+
+	// Non-Windows: nothing to do automatically — inform the user.
+	slog.Info("update downloaded — please run the installer manually", "path", installerPath)
+	return nil
+}
+
+// CompareVersions compares two semver strings (major.minor.patch).
+// Returns -1 if a < b, 0 if equal, 1 if a > b.
+// Strings are trimmed of a leading "v" prefix.
+func CompareVersions(a, b string) int {
+	a = strings.TrimPrefix(a, "v")
+	b = strings.TrimPrefix(b, "v")
+
+	aParts := parseSemver(a)
+	bParts := parseSemver(b)
+
+	for i := 0; i < 3; i++ {
+		if aParts[i] < bParts[i] {
+			return -1
+		}
+		if aParts[i] > bParts[i] {
+			return 1
+		}
+	}
+	return 0
+}
+
+// parseSemver splits a version string into [major, minor, patch].
+// Missing components default to 0.
+func parseSemver(v string) [3]int {
+	var parts [3]int
+	segments := strings.SplitN(v, ".", 3)
+	for i, s := range segments {
+		if i >= 3 {
+			break
+		}
+		n, _ := strconv.Atoi(s)
+		parts[i] = n
+	}
+	return parts
+}
diff --git a/internal/updater/service_test.go b/internal/updater/service_test.go
new file mode 100644
index 0000000..606332e
--- /dev/null
+++ b/internal/updater/service_test.go
@@ -0,0 +1,223 @@
+package updater
+
+import (
+	"encoding/json"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+)
+
+func TestNewUpdateService(t *testing.T) {
+	svc := NewUpdateService("0.2.0")
+	if svc.currentVersion != "0.2.0" {
+		t.Errorf("currentVersion = %q, want %q", svc.currentVersion, "0.2.0")
+	}
+	if svc.baseURL == "" {
+		t.Error("baseURL should not be empty")
+	}
+	if svc.owner == "" {
+		t.Error("owner should not be empty")
+	}
+	if svc.pkg == "" {
+		t.Error("pkg should not be empty")
+	}
+	if svc.httpClient == nil {
+		t.Error("httpClient should not be nil")
+	}
+}
+
+func TestNewUpdateServiceStripsVPrefix(t *testing.T) {
+	svc := NewUpdateService("v1.2.3")
+	if svc.currentVersion != "1.2.3" {
+		t.Errorf("currentVersion = %q, want %q", svc.currentVersion, "1.2.3")
+	}
+}
+
+func TestCompareVersions(t *testing.T) {
+	tests := []struct {
+		a, b string
+		want int
+	}{
+		{"0.2.0", "0.2.1", -1},
+		{"0.2.1", "0.2.0", 1},
+		{"0.3.0", "0.2.9", 1},
+		{"0.2.9", "0.3.0", -1},
+		{"1.0.0", "0.9.9", 1},
+		{"0.9.9", "1.0.0", -1},
+		{"1.0.0", "1.0.0", 0},
+		{"0.0.1", "0.0.1", 0},
+		{"2.0.0", "1.99.99", 1},
+		{"0.1.0", "0.0.99", 1},
+		// With "v" prefix
+		{"v0.2.0", "v0.2.1", -1},
+		{"v1.0.0", "1.0.0", 0},
+	}
+
+	for _, tt := range tests {
+		got := CompareVersions(tt.a, tt.b)
+		if got != tt.want {
+			t.Errorf("CompareVersions(%q, %q) = %d, want %d", tt.a, tt.b, got, tt.want)
+		}
+	}
+}
+
+func TestParseSemver(t *testing.T) {
+	tests := []struct {
+		input string
+		want  [3]int
+	}{
+		{"1.2.3", [3]int{1, 2, 3}},
+		{"0.0.0", [3]int{0, 0, 0}},
+		{"10.20.30", [3]int{10, 20, 30}},
+		{"1.2", [3]int{1, 2, 0}},
+		{"1", [3]int{1, 0, 0}},
+		{"", [3]int{0, 0, 0}},
+	}
+
+	for _, tt := range tests {
+		got := parseSemver(tt.input)
+		if got != tt.want {
+			t.Errorf("parseSemver(%q) = %v, want %v", tt.input, got, tt.want)
+		}
+	}
+}
+
+func TestParseVersionJSON(t *testing.T) {
+	raw := `{"version":"0.3.0","sha256":"abcdef1234567890","downloadUrl":"https://example.com/setup.exe"}`
+	var v versionJSON
+	if err := json.Unmarshal([]byte(raw), &v); err != nil {
+		t.Fatalf("Unmarshal error: %v", err)
+	}
+	if v.Version != "0.3.0" {
+		t.Errorf("Version = %q, want %q", v.Version, "0.3.0")
+	}
+	if v.SHA256 != "abcdef1234567890" {
+		t.Errorf("SHA256 = %q, want %q", v.SHA256, "abcdef1234567890")
+	}
+	if v.DownloadURL != "https://example.com/setup.exe" {
+		t.Errorf("DownloadURL = %q, want %q", v.DownloadURL, "https://example.com/setup.exe")
+	}
+}
+
+func TestCheckForUpdate_NewerAvailable(t *testing.T) {
+	// Mock the Gitea API: return a single package version that is newer.
+	mux := http.NewServeMux()
+	mux.HandleFunc("/api/v1/packages/vstockwell/generic/wraith", func(w http.ResponseWriter, r *http.Request) {
+		versions := []giteaPackageVersion{{Version: "0.3.0"}}
+		w.Header().Set("Content-Type", "application/json")
+		json.NewEncoder(w).Encode(versions)
+	})
+	mux.HandleFunc("/api/packages/vstockwell/generic/wraith/0.3.0/version.json", func(w http.ResponseWriter, r *http.Request) {
+		v := versionJSON{
+			Version:     "0.3.0",
+			SHA256:      "abc123",
+			DownloadURL: "https://example.com/wraith-0.3.0-setup.exe",
+		}
+		w.Header().Set("Content-Type", "application/json")
+		json.NewEncoder(w).Encode(v)
+	})
+	server := httptest.NewServer(mux)
+	defer server.Close()
+
+	svc := NewUpdateService("0.2.0")
+	svc.baseURL = server.URL
+
+	info, err := svc.CheckForUpdate()
+	if err != nil {
+		t.Fatalf("CheckForUpdate() error: %v", err)
+	}
+	if !info.Available {
+		t.Error("expected Available = true")
+	}
+	if info.LatestVer != "0.3.0" {
+		t.Errorf("LatestVer = %q, want %q", info.LatestVer, "0.3.0")
+	}
+	if info.SHA256 != "abc123" {
+		t.Errorf("SHA256 = %q, want %q", info.SHA256, "abc123")
+	}
+	if info.DownloadURL != "https://example.com/wraith-0.3.0-setup.exe" {
+		t.Errorf("DownloadURL = %q, want %q", info.DownloadURL, "https://example.com/wraith-0.3.0-setup.exe")
+	}
+}
+
+func TestCheckForUpdate_AlreadyUpToDate(t *testing.T) {
+	mux := http.NewServeMux()
+	mux.HandleFunc("/api/v1/packages/vstockwell/generic/wraith", func(w http.ResponseWriter, r *http.Request) {
+		versions := []giteaPackageVersion{{Version: "0.2.0"}}
+		w.Header().Set("Content-Type", "application/json")
+		json.NewEncoder(w).Encode(versions)
+	})
+	server := httptest.NewServer(mux)
+	defer server.Close()
+
+	svc := NewUpdateService("0.2.0")
+	svc.baseURL = server.URL
+
+	info, err := svc.CheckForUpdate()
+	if err != nil {
+		t.Fatalf("CheckForUpdate() error: %v", err)
+	}
+	if info.Available {
+		t.Error("expected Available = false (same version)")
+	}
+}
+
+func TestCheckForUpdate_CurrentIsNewer(t *testing.T) {
+	mux := http.NewServeMux()
+	mux.HandleFunc("/api/v1/packages/vstockwell/generic/wraith", func(w http.ResponseWriter, r *http.Request) {
+		versions := []giteaPackageVersion{{Version: "0.1.0"}}
+		w.Header().Set("Content-Type", "application/json")
+		json.NewEncoder(w).Encode(versions)
+	})
+	server := httptest.NewServer(mux)
+	defer server.Close()
+
+	svc := NewUpdateService("0.2.0")
+	svc.baseURL = server.URL
+
+	info, err := svc.CheckForUpdate()
+	if err != nil {
+		t.Fatalf("CheckForUpdate() error: %v", err)
+	}
+	if info.Available {
+		t.Error("expected Available = false (current is newer)")
+	}
+}
+
+func TestCheckForUpdate_NoVersions(t *testing.T) {
+	mux := http.NewServeMux()
+	mux.HandleFunc("/api/v1/packages/vstockwell/generic/wraith", func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		json.NewEncoder(w).Encode([]giteaPackageVersion{})
+	})
+	server := httptest.NewServer(mux)
+	defer server.Close()
+
+	svc := NewUpdateService("0.2.0")
+	svc.baseURL = server.URL
+
+	info, err := svc.CheckForUpdate()
+	if err != nil {
+		t.Fatalf("CheckForUpdate() error: %v", err)
+	}
+	if info.Available {
+		t.Error("expected Available = false (no versions)")
+	}
+}
+
+func TestCheckForUpdate_APIError(t *testing.T) {
+	mux := http.NewServeMux()
+	mux.HandleFunc("/api/v1/packages/vstockwell/generic/wraith", func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusInternalServerError)
+	})
+	server := httptest.NewServer(mux)
+	defer server.Close()
+
+	svc := NewUpdateService("0.2.0")
+	svc.baseURL = server.URL
+
+	_, err := svc.CheckForUpdate()
+	if err == nil {
+		t.Error("expected error from API failure")
+	}
+}
diff --git a/main.go b/main.go
index 603a826..4ed045e 100644
--- a/main.go
+++ b/main.go
@@ -18,7 +18,7 @@ var assets embed.FS
 func main() {
 	slog.Info("starting Wraith")
 
-	wraith, err := wraithapp.New()
+	wraith, err := wraithapp.New(version)
 	if err != nil {
 		log.Fatalf("failed to initialize: %v", err)
 	}
@@ -35,6 +35,7 @@ func main() {
 			application.NewService(wraith.SFTP),
 			application.NewService(wraith.RDP),
 			application.NewService(wraith.AI),
+			application.NewService(wraith.Updater),
 		},
 		Assets: application.AssetOptions{
 			Handler: application.BundledAssetFileServer(assets),