feat: Overhaul Docker infrastructure with multi-stage builds, add a cleanup script, and refactor the update service to combine update and requirement checks.

shared/modules/admin/update.service.test.ts

@@ -1,5 +1,4 @@
-import { describe, expect, test, mock, beforeEach, afterAll, spyOn } from "bun:test";
-import * as fs from "fs/promises";
+import { describe, expect, test, mock, beforeEach, afterAll } from "bun:test";
 
 // Mock child_process BEFORE importing the service
 const mockExec = mock((cmd: string, callback?: any) => {
@@ -8,23 +7,32 @@ const mockExec = mock((cmd: string, callback?: any) => {
         return { unref: () => { } };
     }
 
-    if (cmd.includes("git rev-parse")) {
-        callback(null, { stdout: "main\n" });
+    // Simulate successful command execution
+    let stdout = "";
+    
+    if (cmd.includes("git rev-parse --abbrev-ref")) {
+        stdout = "main\n";
+    } else if (cmd.includes("git rev-parse --short")) {
+        stdout = "abc1234\n";
+    } else if (cmd.includes("git rev-parse HEAD")) {
+        stdout = "abc1234567890\n";
     } else if (cmd.includes("git fetch")) {
-        callback(null, { stdout: "" });
+        stdout = "";
     } else if (cmd.includes("git log")) {
-        callback(null, { stdout: "abcdef Update 1\n123456 Update 2" });
+        stdout = "abcdef|Update 1|Author1\n123456|Update 2|Author2";
     } else if (cmd.includes("git diff")) {
-        callback(null, { stdout: "package.json\nsrc/index.ts" });
+        stdout = "package.json\nsrc/index.ts\nshared/lib/schema.ts";
     } else if (cmd.includes("git reset")) {
-        callback(null, { stdout: "HEAD is now at abcdef Update 1" });
+        stdout = "HEAD is now at abcdef Update 1";
     } else if (cmd.includes("bun install")) {
-        callback(null, { stdout: "Installed dependencies" });
+        stdout = "Installed dependencies";
     } else if (cmd.includes("drizzle-kit migrate")) {
-        callback(null, { stdout: "Migrations applied" });
-    } else {
-        callback(null, { stdout: "" });
+        stdout = "Migrations applied";
+    } else if (cmd.includes("bun run build")) {
+        stdout = "Build completed";
     }
+
+    callback(null, stdout, "");
 });
 
 mock.module("child_process", () => ({
@@ -32,9 +40,9 @@ mock.module("child_process", () => ({
 }));
 
 // Mock fs/promises
-const mockWriteFile = mock((path: string, content: string) => Promise.resolve());
-const mockReadFile = mock((path: string, encoding: string) => Promise.resolve("{}"));
-const mockUnlink = mock((path: string) => Promise.resolve());
+const mockWriteFile = mock((_path: string, _content: string) => Promise.resolve());
+const mockReadFile = mock((_path: string, _encoding: string) => Promise.resolve("{}"));
+const mockUnlink = mock((_path: string) => Promise.resolve());
 
 mock.module("fs/promises", () => ({
     writeFile: mockWriteFile,
@@ -43,9 +51,9 @@ mock.module("fs/promises", () => ({
 }));
 
 // Mock view module to avoid import issues
-mock.module("./update.view", () => ({
-    getPostRestartEmbed: () => ({ title: "Update Complete" }),
-    getInstallingDependenciesEmbed: () => ({ title: "Installing..." }),
+mock.module("@/modules/admin/update.view", () => ({
+    getPostRestartEmbed: () => ({ embeds: [{ title: "Update Complete" }], components: [] }),
+    getPostRestartProgressEmbed: () => ({ title: "Progress..." }),
 }));
 
 describe("UpdateService", () => {
@@ -72,7 +80,8 @@ describe("UpdateService", () => {
 
             expect(result.hasUpdates).toBe(true);
             expect(result.branch).toBe("main");
-            expect(result.log).toContain("Update 1");
+            expect(result.commits.length).toBeGreaterThan(0);
+            expect(result.commits[0].message).toContain("Update 1");
         });
 
         test("should call git rev-parse, fetch, and log commands", async () => {
@@ -83,43 +92,82 @@ describe("UpdateService", () => {
             expect(calls.some((cmd: string) => cmd.includes("git fetch"))).toBe(true);
             expect(calls.some((cmd: string) => cmd.includes("git log"))).toBe(true);
         });
+
+        test("should include requirements in the response", async () => {
+            const result = await UpdateService.checkForUpdates();
+
+            expect(result.requirements).toBeDefined();
+            expect(result.requirements.needsRootInstall).toBe(true); // package.json is in mock
+            expect(result.requirements.needsMigrations).toBe(true); // schema.ts is in mock
+            expect(result.requirements.changedFiles).toContain("package.json");
+        });
     });
 
     describe("performUpdate", () => {
         test("should run git reset --hard with correct branch", async () => {
             await UpdateService.performUpdate("main");
 
-            const lastCall = mockExec.mock.lastCall;
-            expect(lastCall).toBeDefined();
-            expect(lastCall![0]).toContain("git reset --hard origin/main");
+            const calls = mockExec.mock.calls.map((c: any) => c[0]);
+            expect(calls.some((cmd: string) => cmd.includes("git reset --hard origin/main"))).toBe(true);
         });
     });
 
-    describe("checkUpdateRequirements", () => {
+    describe("checkUpdateRequirements (deprecated)", () => {
         test("should detect package.json and schema.ts changes", async () => {
             const result = await UpdateService.checkUpdateRequirements("main");
 
-            expect(result.needsInstall).toBe(true);
-            expect(result.needsMigrations).toBe(false); // mock doesn't include schema.ts
+            expect(result.needsRootInstall).toBe(true);
+            expect(result.needsMigrations).toBe(true);
             expect(result.error).toBeUndefined();
         });
 
         test("should call git diff with correct branch", async () => {
             await UpdateService.checkUpdateRequirements("develop");
 
-            const lastCall = mockExec.mock.lastCall;
-            expect(lastCall).toBeDefined();
-            expect(lastCall![0]).toContain("git diff HEAD..origin/develop");
+            const calls = mockExec.mock.calls.map((c: any) => c[0]);
+            expect(calls.some((cmd: string) => cmd.includes("git diff HEAD..origin/develop"))).toBe(true);
         });
     });
 
     describe("installDependencies", () => {
-        test("should run bun install and return output", async () => {
-            const output = await UpdateService.installDependencies();
+        test("should run bun install for root only", async () => {
+            const output = await UpdateService.installDependencies({ root: true, web: false });
 
-            expect(output).toBe("Installed dependencies");
-            const lastCall = mockExec.mock.lastCall;
-            expect(lastCall![0]).toBe("bun install");
+            expect(output).toContain("Root");
+            const calls = mockExec.mock.calls.map((c: any) => c[0]);
+            expect(calls.some((cmd: string) => cmd === "bun install")).toBe(true);
+        });
+
+        test("should run bun install for both root and web in parallel", async () => {
+            const output = await UpdateService.installDependencies({ root: true, web: true });
+
+            expect(output).toContain("Root");
+            expect(output).toContain("Web");
+            const calls = mockExec.mock.calls.map((c: any) => c[0]);
+            expect(calls.some((cmd: string) => cmd === "bun install")).toBe(true);
+            expect(calls.some((cmd: string) => cmd.includes("cd web && bun install"))).toBe(true);
+        });
+    });
+
+    describe("categorizeChanges", () => {
+        test("should categorize files correctly", () => {
+            const files = [
+                "bot/commands/admin/update.ts",
+                "bot/modules/admin/update.view.ts",
+                "web/src/components/Button.tsx",
+                "shared/lib/utils.ts",
+                "package.json",
+                "drizzle/0001_migration.sql"
+            ];
+
+            const categories = UpdateService.categorizeChanges(files);
+
+            expect(categories["Commands"]).toBe(1);
+            expect(categories["Modules"]).toBe(1);
+            expect(categories["Web Dashboard"]).toBe(1);
+            expect(categories["Library"]).toBe(1);
+            expect(categories["Dependencies"]).toBe(1);
+            expect(categories["Database"]).toBe(1);
         });
     });
 
@@ -130,7 +178,10 @@ describe("UpdateService", () => {
                 userId: "456",
                 timestamp: Date.now(),
                 runMigrations: true,
-                installDependencies: false
+                installDependencies: false,
+                buildWebAssets: false,
+                previousCommit: "abc1234",
+                newCommit: "def5678"
             };
 
             await UpdateService.prepareRestartContext(context);
@@ -143,6 +194,39 @@ describe("UpdateService", () => {
         });
     });
 
+    describe("saveRollbackPoint", () => {
+        test("should save current commit hash to file", async () => {
+            const commit = await UpdateService.saveRollbackPoint();
+
+            expect(commit).toBeTruthy();
+            expect(mockWriteFile).toHaveBeenCalled();
+            const lastCall = mockWriteFile.mock.lastCall as [string, string] | undefined;
+            expect(lastCall![0]).toContain("rollback_commit");
+        });
+    });
+
+    describe("hasRollbackPoint", () => {
+        test("should return true when rollback file exists", async () => {
+            mockReadFile.mockImplementationOnce(() => Promise.resolve("abc123"));
+            
+            // Clear cache first
+            (UpdateService as any).rollbackPointExists = null;
+            
+            const result = await UpdateService.hasRollbackPoint();
+            expect(result).toBe(true);
+        });
+
+        test("should return false when rollback file does not exist", async () => {
+            mockReadFile.mockImplementationOnce(() => Promise.reject(new Error("ENOENT")));
+            
+            // Clear cache first
+            (UpdateService as any).rollbackPointExists = null;
+            
+            const result = await UpdateService.hasRollbackPoint();
+            expect(result).toBe(false);
+        });
+    });
+
     describe("triggerRestart", () => {
         test("should use RESTART_COMMAND env var when set", async () => {
             const originalEnv = process.env.RESTART_COMMAND;
@@ -150,24 +234,19 @@ describe("UpdateService", () => {
 
             await UpdateService.triggerRestart();
 
-            const lastCall = mockExec.mock.lastCall;
-            expect(lastCall).toBeDefined();
-            expect(lastCall![0]).toBe("pm2 restart bot");
+            const calls = mockExec.mock.calls.map((c: any) => c[0]);
+            expect(calls.some((cmd: string) => cmd === "pm2 restart bot")).toBe(true);
 
             process.env.RESTART_COMMAND = originalEnv;
         });
 
-        test("should write to trigger file when no env var", async () => {
+        test("should call process.exit when no env var is set", async () => {
             const originalEnv = process.env.RESTART_COMMAND;
             delete process.env.RESTART_COMMAND;
 
+            // Just verify it doesn't throw - actual process.exit is mocked by setTimeout
             await UpdateService.triggerRestart();
 
-            expect(mockWriteFile).toHaveBeenCalled();
-            const lastCall = mockWriteFile.mock.lastCall as [string, string] | undefined;
-            expect(lastCall).toBeDefined();
-            expect(lastCall![0]).toContain("restart_trigger");
-
             process.env.RESTART_COMMAND = originalEnv;
         });
     });
@@ -181,7 +260,7 @@ describe("UpdateService", () => {
 
         const createMockChannel = () => ({
             isSendable: () => true,
-            send: mock(() => Promise.resolve())
+            send: mock(() => Promise.resolve({ edit: mock(() => Promise.resolve()), delete: mock(() => Promise.resolve()) }))
         });
 
         test("should ignore stale context (>10 mins old)", async () => {
@@ -190,7 +269,10 @@ describe("UpdateService", () => {
                 userId: "456",
                 timestamp: Date.now() - (15 * 60 * 1000), // 15 mins ago
                 runMigrations: true,
-                installDependencies: true
+                installDependencies: true,
+                buildWebAssets: false,
+                previousCommit: "abc",
+                newCommit: "def"
             };
 
             mockReadFile.mockImplementationOnce(() => Promise.resolve(JSON.stringify(staleContext)));
@@ -227,7 +309,10 @@ describe("UpdateService", () => {
                 userId: "456",
                 timestamp: Date.now(),
                 runMigrations: false,
-                installDependencies: false
+                installDependencies: false,
+                buildWebAssets: false,
+                previousCommit: "abc",
+                newCommit: "def"
             };
 
             mockReadFile.mockImplementationOnce(() => Promise.resolve(JSON.stringify(validContext)));
@@ -236,7 +321,7 @@ describe("UpdateService", () => {
             const { TextChannel } = await import("discord.js");
             const mockChannel = Object.create(TextChannel.prototype);
             mockChannel.isSendable = () => true;
-            mockChannel.send = mock(() => Promise.resolve());
+            mockChannel.send = mock(() => Promise.resolve({ edit: mock(() => Promise.resolve()), delete: mock(() => Promise.resolve()) }));
 
             const mockClient = createMockClient(mockChannel);
 

shared/modules/admin/update.service.ts

@@ -1,4 +1,4 @@
-import { exec } from "child_process";
+import { exec, type ExecException } from "child_process";
 import { promisify } from "util";
 import { writeFile, readFile, unlink } from "fs/promises";
 import { Client, TextChannel } from "discord.js";
@@ -10,32 +10,69 @@ const execAsync = promisify(exec);
 
 // Constants
 const STALE_CONTEXT_MS = 10 * 60 * 1000; // 10 minutes
+const DEFAULT_TIMEOUT_MS = 30_000; // 30 seconds for git commands
+const INSTALL_TIMEOUT_MS = 120_000; // 2 minutes for dependency installation
+const BUILD_TIMEOUT_MS = 180_000; // 3 minutes for web build
 
+/**
+ * Execute a command with timeout protection
+ */
+async function execWithTimeout(
+    cmd: string,
+    timeoutMs: number = DEFAULT_TIMEOUT_MS
+): Promise<{ stdout: string; stderr: string }> {
+    return new Promise((resolve, reject) => {
+        const process = exec(cmd, (error: ExecException | null, stdout: string, stderr: string) => {
+            if (error) {
+                reject(error);
+            } else {
+                resolve({ stdout, stderr });
+            }
+        });
 
+        const timer = setTimeout(() => {
+            process.kill("SIGTERM");
+            reject(new Error(`Command timed out after ${timeoutMs}ms: ${cmd}`));
+        }, timeoutMs);
+
+        process.on("exit", () => clearTimeout(timer));
+    });
+}
 
 export class UpdateService {
     private static readonly CONTEXT_FILE = ".restart_context.json";
     private static readonly ROLLBACK_FILE = ".rollback_commit.txt";
 
+    // Cache for rollback state (set when we save, cleared on cleanup)
+    private static rollbackPointExists: boolean | null = null;
+
     /**
      * Check for available updates with detailed commit information
+     * Optimized: Parallel git commands and combined requirements check
      */
-    static async checkForUpdates(): Promise<UpdateInfo> {
-        const { stdout: branchName } = await execAsync("git rev-parse --abbrev-ref HEAD");
+    static async checkForUpdates(): Promise<UpdateInfo & { requirements: UpdateCheckResult }> {
+        // Get branch first (needed for subsequent commands)
+        const { stdout: branchName } = await execWithTimeout("git rev-parse --abbrev-ref HEAD");
         const branch = branchName.trim();
 
-        const { stdout: currentCommit } = await execAsync("git rev-parse --short HEAD");
+        // Parallel execution: get current commit while fetching
+        const [currentResult] = await Promise.all([
+            execWithTimeout("git rev-parse --short HEAD"),
+            execWithTimeout(`git fetch origin ${branch} --prune`) // Only fetch current branch
+        ]);
+        const currentCommit = currentResult.stdout.trim();
 
-        await execAsync("git fetch --all");
+        // After fetch completes, get remote info in parallel
+        const [latestResult, logResult, diffResult] = await Promise.all([
+            execWithTimeout(`git rev-parse --short origin/${branch}`),
+            execWithTimeout(`git log HEAD..origin/${branch} --format="%h|%s|%an" --no-merges`),
+            execWithTimeout(`git diff HEAD..origin/${branch} --name-only`)
+        ]);
 
-        const { stdout: latestCommit } = await execAsync(`git rev-parse --short origin/${branch}`);
+        const latestCommit = latestResult.stdout.trim();
 
-        // Get commit log with author info
-        const { stdout: logOutput } = await execAsync(
-            `git log HEAD..origin/${branch} --format="%h|%s|%an" --no-merges`
-        );
-
-        const commits: CommitInfo[] = logOutput
+        // Parse commit log
+        const commits: CommitInfo[] = logResult.stdout
             .trim()
             .split("\n")
             .filter(line => line.length > 0)
@@ -44,51 +81,64 @@ export class UpdateService {
                 return { hash: hash || "", message: message || "", author: author || "" };
             });
 
+        // Parse changed files and analyze requirements in one pass
+        const changedFiles = diffResult.stdout.trim().split("\n").filter(f => f.length > 0);
+        const requirements = this.analyzeChangedFiles(changedFiles);
+
         return {
             hasUpdates: commits.length > 0,
             branch,
-            currentCommit: currentCommit.trim(),
-            latestCommit: latestCommit.trim(),
+            currentCommit,
+            latestCommit,
             commitCount: commits.length,
-            commits
+            commits,
+            requirements
         };
     }
 
     /**
-     * Analyze what the update requires
+     * Analyze changed files to determine update requirements
+     * Extracted for reuse and clarity
+     */
+    private static analyzeChangedFiles(changedFiles: string[]): UpdateCheckResult {
+        const needsRootInstall = changedFiles.some(file =>
+            file === "package.json" || file === "bun.lock"
+        );
+
+        const needsWebInstall = changedFiles.some(file =>
+            file === "web/package.json" || file === "web/bun.lock"
+        );
+
+        // Only rebuild web if essential source files changed
+        const needsWebBuild = changedFiles.some(file =>
+            file.match(/^web\/src\/(components|pages|lib|index)/) ||
+            file === "web/build.ts" ||
+            file === "web/tailwind.config.ts" ||
+            file === "web/tsconfig.json"
+        );
+
+        const needsMigrations = changedFiles.some(file =>
+            file.includes("schema.ts") || file.startsWith("drizzle/")
+        );
+
+        return {
+            needsRootInstall,
+            needsWebInstall,
+            needsWebBuild,
+            needsMigrations,
+            changedFiles
+        };
+    }
+
+    /**
+     * @deprecated Use checkForUpdates() which now includes requirements
+     * Kept for backwards compatibility
      */
     static async checkUpdateRequirements(branch: string): Promise<UpdateCheckResult> {
         try {
-            const { stdout } = await execAsync(`git diff HEAD..origin/${branch} --name-only`);
+            const { stdout } = await execWithTimeout(`git diff HEAD..origin/${branch} --name-only`);
             const changedFiles = stdout.trim().split("\n").filter(f => f.length > 0);
-
-            const needsRootInstall = changedFiles.some(file =>
-                file === "package.json" || file === "bun.lock"
-            );
-
-            const needsWebInstall = changedFiles.some(file =>
-                file === "web/package.json" || file === "web/bun.lock"
-            );
-
-            // Detect if web source files changed (requires rebuild)
-            const needsWebBuild = changedFiles.some(file =>
-                file.startsWith("web/src/") ||
-                file === "web/build.ts" ||
-                file === "web/tailwind.config.ts" ||
-                file === "web/tsconfig.json"
-            );
-
-            const needsMigrations = changedFiles.some(file =>
-                file.includes("schema.ts") || file.startsWith("drizzle/")
-            );
-
-            return {
-                needsRootInstall,
-                needsWebInstall,
-                needsWebBuild,
-                needsMigrations,
-                changedFiles
-            };
+            return this.analyzeChangedFiles(changedFiles);
         } catch (e) {
             console.error("Failed to check update requirements:", e);
             return {
@@ -129,9 +179,10 @@ export class UpdateService {
      * Save the current commit for potential rollback
      */
     static async saveRollbackPoint(): Promise<string> {
-        const { stdout } = await execAsync("git rev-parse HEAD");
+        const { stdout } = await execWithTimeout("git rev-parse HEAD");
         const commit = stdout.trim();
         await writeFile(this.ROLLBACK_FILE, commit);
+        this.rollbackPointExists = true; // Cache the state
         return commit;
     }
 
@@ -141,8 +192,9 @@ export class UpdateService {
     static async rollback(): Promise<{ success: boolean; message: string }> {
         try {
             const rollbackCommit = await readFile(this.ROLLBACK_FILE, "utf-8");
-            await execAsync(`git reset --hard ${rollbackCommit.trim()}`);
+            await execWithTimeout(`git reset --hard ${rollbackCommit.trim()}`);
             await unlink(this.ROLLBACK_FILE);
+            this.rollbackPointExists = false;
             return { success: true, message: `Rolled back to ${rollbackCommit.trim().substring(0, 7)}` };
         } catch (e) {
             return {
@@ -154,12 +206,18 @@ export class UpdateService {
 
     /**
      * Check if a rollback point exists
+     * Uses cache when available to avoid file system access
      */
     static async hasRollbackPoint(): Promise<boolean> {
+        if (this.rollbackPointExists !== null) {
+            return this.rollbackPointExists;
+        }
         try {
             await readFile(this.ROLLBACK_FILE, "utf-8");
+            this.rollbackPointExists = true;
             return true;
         } catch {
+            this.rollbackPointExists = false;
             return false;
         }
     }
@@ -168,26 +226,32 @@ export class UpdateService {
      * Perform the git update
      */
     static async performUpdate(branch: string): Promise<void> {
-        await execAsync(`git reset --hard origin/${branch}`);
+        await execWithTimeout(`git reset --hard origin/${branch}`);
     }
 
     /**
      * Install dependencies for specified projects
+     * Optimized: Parallel installation
      */
     static async installDependencies(options: { root: boolean; web: boolean }): Promise<string> {
-        const outputs: string[] = [];
+        const tasks: Promise<{ label: string; output: string }>[] = [];
 
         if (options.root) {
-            const { stdout } = await execAsync("bun install");
-            outputs.push(`📦 Root: ${stdout.trim() || "Done"}`);
+            tasks.push(
+                execWithTimeout("bun install", INSTALL_TIMEOUT_MS)
+                    .then(({ stdout }) => ({ label: "📦 Root", output: stdout.trim() || "Done" }))
+            );
         }
 
         if (options.web) {
-            const { stdout } = await execAsync("cd web && bun install");
-            outputs.push(`🌐 Web: ${stdout.trim() || "Done"}`);
+            tasks.push(
+                execWithTimeout("cd web && bun install", INSTALL_TIMEOUT_MS)
+                    .then(({ stdout }) => ({ label: "🌐 Web", output: stdout.trim() || "Done" }))
+            );
         }
 
-        return outputs.join("\n");
+        const results = await Promise.all(tasks);
+        return results.map(r => `${r.label}: ${r.output}`).join("\n");
     }
 
     /**
@@ -228,7 +292,7 @@ export class UpdateService {
             }
 
             const result = await this.executePostRestartTasks(context, channel);
-            await this.notifyPostRestartResult(channel, result, context);
+            await this.notifyPostRestartResult(channel, result);
             await this.cleanupContext();
         } catch (e) {
             console.error("Failed to handle post-restart context:", e);
@@ -301,21 +365,33 @@ export class UpdateService {
             }
         };
 
-        // 1. Install Dependencies if needed
+        // 1. Install Dependencies if needed (PARALLELIZED)
         if (context.installDependencies) {
             try {
                 progress.currentStep = "install";
                 await updateProgress();
 
-                const { stdout: rootOutput } = await execAsync("bun install");
-                const { stdout: webOutput } = await execAsync("cd web && bun install");
+                // Parallel installation of root and web dependencies
+                const [rootResult, webResult] = await Promise.all([
+                    execWithTimeout("bun install", INSTALL_TIMEOUT_MS)
+                        .then(({ stdout }) => ({ success: true, output: stdout.trim() || "Done" }))
+                        .catch(err => ({ success: false, output: err instanceof Error ? err.message : String(err) })),
+                    execWithTimeout("cd web && bun install", INSTALL_TIMEOUT_MS)
+                        .then(({ stdout }) => ({ success: true, output: stdout.trim() || "Done" }))
+                        .catch(err => ({ success: false, output: err instanceof Error ? err.message : String(err) }))
+                ]);
 
-                result.installOutput = `📦 Root: ${rootOutput.trim() || "Done"}\n🌐 Web: ${webOutput.trim() || "Done"}`;
+                result.installSuccess = rootResult.success && webResult.success;
+                result.installOutput = `📦 Root: ${rootResult.output}\n🌐 Web: ${webResult.output}`;
                 progress.installDone = true;
+
+                if (!result.installSuccess) {
+                    console.error("Dependency Install Failed:", result.installOutput);
+                }
             } catch (err: unknown) {
                 result.installSuccess = false;
                 result.installOutput = err instanceof Error ? err.message : String(err);
-                progress.installDone = true; // Mark as done even on failure
+                progress.installDone = true;
                 console.error("Dependency Install Failed:", err);
             }
         }
@@ -326,7 +402,7 @@ export class UpdateService {
                 progress.currentStep = "build";
                 await updateProgress();
 
-                const { stdout } = await execAsync("cd web && bun run build");
+                const { stdout } = await execWithTimeout("cd web && bun run build", BUILD_TIMEOUT_MS);
                 result.webBuildOutput = stdout.trim() || "Build completed successfully";
                 progress.buildDone = true;
             } catch (err: unknown) {
@@ -343,7 +419,7 @@ export class UpdateService {
                 progress.currentStep = "migrate";
                 await updateProgress();
 
-                const { stdout } = await execAsync("bun x drizzle-kit migrate");
+                const { stdout } = await execWithTimeout("bun x drizzle-kit migrate", DEFAULT_TIMEOUT_MS);
                 result.migrationOutput = stdout;
                 progress.migrateDone = true;
             } catch (err: unknown) {
@@ -368,9 +444,9 @@ export class UpdateService {
 
     private static async notifyPostRestartResult(
         channel: TextChannel,
-        result: PostRestartResult,
-        context: RestartContext
+        result: PostRestartResult
     ): Promise<void> {
+        // Use cached rollback state - we just saved it before restart
         const hasRollback = await this.hasRollbackPoint();
         await channel.send(getPostRestartEmbed(result, hasRollback));
     }
@@ -381,5 +457,6 @@ export class UpdateService {
         } catch {
             // File may not exist, ignore
         }
+        // Don't clear rollback cache here - rollback file persists
     }
 }