diff --git a/bot/commands/admin/update.ts b/bot/commands/admin/update.ts
index 90a5340..f0598e5 100644
--- a/bot/commands/admin/update.ts
+++ b/bot/commands/admin/update.ts
@@ -97,6 +97,7 @@ async function handleUpdate(interaction: any) {
                     timestamp: Date.now(),
                     runMigrations: requirements.needsMigrations,
                     installDependencies: requirements.needsRootInstall || requirements.needsWebInstall,
+                    buildWebAssets: requirements.needsWebBuild,
                     previousCommit: previousCommit.substring(0, 7),
                     newCommit: updateInfo.latestCommit
                 });
diff --git a/bot/modules/admin/update.types.ts b/bot/modules/admin/update.types.ts
index 633a6ad..8098d38 100644
--- a/bot/modules/admin/update.types.ts
+++ b/bot/modules/admin/update.types.ts
@@ -5,6 +5,7 @@ export interface RestartContext {
     timestamp: number;
     runMigrations: boolean;
     installDependencies: boolean;
+    buildWebAssets: boolean;
     previousCommit: string;
     newCommit: string;
 }
@@ -12,6 +13,7 @@ export interface RestartContext {
 export interface UpdateCheckResult {
     needsRootInstall: boolean;
     needsWebInstall: boolean;
+    needsWebBuild: boolean;
     needsMigrations: boolean;
     changedFiles: string[];
     error?: Error;
diff --git a/bot/modules/admin/update.view.ts b/bot/modules/admin/update.view.ts
index 734d37b..bb74e53 100644
--- a/bot/modules/admin/update.view.ts
+++ b/bot/modules/admin/update.view.ts
@@ -31,7 +31,7 @@ export function getUpdatesAvailableMessage(
     force: boolean
 ) {
     const { branch, currentCommit, latestCommit, commitCount, commits } = updateInfo;
-    const { needsRootInstall, needsWebInstall, needsMigrations } = requirements;
+    const { needsRootInstall, needsWebInstall, needsWebBuild, needsMigrations } = requirements;
 
     // Build commit list (max 5)
     const commitList = commits
@@ -50,6 +50,7 @@ export function getUpdatesAvailableMessage(
     const reqs: string[] = [];
     if (needsRootInstall) reqs.push("📦 Install root dependencies");
     if (needsWebInstall) reqs.push("🌐 Install web dependencies");
+    if (needsWebBuild) reqs.push("🏗️ Build web dashboard");
     if (needsMigrations) reqs.push("🗃️ Run database migrations");
     if (reqs.length === 0) reqs.push("⚡ Quick update (no extra steps)");
 
@@ -124,6 +125,9 @@ export function getUpdatingEmbed(requirements: UpdateCheckResult) {
     if (requirements.needsRootInstall || requirements.needsWebInstall) {
         steps.push("📦 Dependencies will be installed after restart");
     }
+    if (requirements.needsWebBuild) {
+        steps.push("🏗️ Web dashboard will be rebuilt after restart");
+    }
     if (requirements.needsMigrations) {
         steps.push("🗃️ Migrations will run after restart");
     }
@@ -157,16 +161,19 @@ export function getErrorEmbed(error: unknown) {
 export interface PostRestartResult {
     installSuccess: boolean;
     installOutput: string;
+    webBuildSuccess: boolean;
+    webBuildOutput: string;
     migrationSuccess: boolean;
     migrationOutput: string;
     ranInstall: boolean;
+    ranWebBuild: boolean;
     ranMigrations: boolean;
     previousCommit?: string;
     newCommit?: string;
 }
 
 export function getPostRestartEmbed(result: PostRestartResult, hasRollback: boolean) {
-    const isSuccess = result.installSuccess && result.migrationSuccess;
+    const isSuccess = result.installSuccess && result.webBuildSuccess && result.migrationSuccess;
 
     const embed = new EmbedBuilder()
         .setTitle(isSuccess ? "✅ Update Complete" : "⚠️ Update Completed with Issues")
@@ -192,6 +199,13 @@ export function getPostRestartEmbed(result: PostRestartResult, hasRollback: bool
         );
     }
 
+    if (result.ranWebBuild) {
+        results.push(result.webBuildSuccess
+            ? "✅ Web dashboard built"
+            : "❌ Web dashboard build failed"
+        );
+    }
+
     if (result.ranMigrations) {
         results.push(result.migrationSuccess
             ? "✅ Migrations applied"
@@ -216,6 +230,14 @@ export function getPostRestartEmbed(result: PostRestartResult, hasRollback: bool
         });
     }
 
+    if (result.webBuildOutput && !result.webBuildSuccess) {
+        embed.addFields({
+            name: "Web Build Output",
+            value: `\`\`\`\n${truncate(result.webBuildOutput, OUTPUT_TRUNCATE_LENGTH)}\n\`\`\``,
+            inline: false
+        });
+    }
+
     if (result.migrationOutput && !result.migrationSuccess) {
         embed.addFields({
             name: "Migration Output",
@@ -259,6 +281,66 @@ export function getRunningMigrationsEmbed() {
     );
 }
 
+export function getBuildingWebEmbed() {
+    return createInfoEmbed(
+        "🌐 Building web dashboard assets...\nThis may take a moment.",
+        "⏳ Building Web Dashboard"
+    );
+}
+
+export interface PostRestartProgress {
+    installDeps: boolean;
+    buildWeb: boolean;
+    runMigrations: boolean;
+    currentStep: "starting" | "install" | "build" | "migrate" | "done";
+    installDone?: boolean;
+    buildDone?: boolean;
+    migrateDone?: boolean;
+}
+
+export function getPostRestartProgressEmbed(progress: PostRestartProgress) {
+    const steps: string[] = [];
+
+    // Installation step
+    if (progress.installDeps) {
+        if (progress.currentStep === "install") {
+            steps.push("⏳ Installing dependencies...");
+        } else if (progress.installDone) {
+            steps.push("✅ Dependencies installed");
+        } else {
+            steps.push("⬚ Install dependencies");
+        }
+    }
+
+    // Web build step
+    if (progress.buildWeb) {
+        if (progress.currentStep === "build") {
+            steps.push("⏳ Building web dashboard...");
+        } else if (progress.buildDone) {
+            steps.push("✅ Web dashboard built");
+        } else {
+            steps.push("⬚ Build web dashboard");
+        }
+    }
+
+    // Migrations step
+    if (progress.runMigrations) {
+        if (progress.currentStep === "migrate") {
+            steps.push("⏳ Running migrations...");
+        } else if (progress.migrateDone) {
+            steps.push("✅ Migrations applied");
+        } else {
+            steps.push("⬚ Run migrations");
+        }
+    }
+
+    if (steps.length === 0) {
+        steps.push("⚡ Quick restart (no extra steps needed)");
+    }
+
+    return createInfoEmbed(steps.join("\n"), "🔄 Post-Update Tasks");
+}
+
 export function getRollbackSuccessEmbed(commit: string) {
     return createSuccessEmbed(
         `Successfully rolled back to commit \`${commit}\`.\nThe bot will restart now.`,
diff --git a/shared/modules/admin/update.service.ts b/shared/modules/admin/update.service.ts
index 2b4f1c2..11e4dcd 100644
--- a/shared/modules/admin/update.service.ts
+++ b/shared/modules/admin/update.service.ts
@@ -2,7 +2,7 @@ import { exec } from "child_process";
 import { promisify } from "util";
 import { writeFile, readFile, unlink } from "fs/promises";
 import { Client, TextChannel } from "discord.js";
-import { getPostRestartEmbed, getInstallingDependenciesEmbed, getRunningMigrationsEmbed } from "@/modules/admin/update.view";
+import { getPostRestartEmbed, getPostRestartProgressEmbed, type PostRestartProgress } from "@/modules/admin/update.view";
 import type { PostRestartResult } from "@/modules/admin/update.view";
 import type { RestartContext, UpdateCheckResult, UpdateInfo, CommitInfo } from "@/modules/admin/update.types";
 
@@ -70,6 +70,14 @@ export class UpdateService {
                 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/")
             );
@@ -77,6 +85,7 @@ export class UpdateService {
             return {
                 needsRootInstall,
                 needsWebInstall,
+                needsWebBuild,
                 needsMigrations,
                 changedFiles
             };
@@ -85,6 +94,7 @@ export class UpdateService {
             return {
                 needsRootInstall: false,
                 needsWebInstall: false,
+                needsWebBuild: false,
                 needsMigrations: false,
                 changedFiles: [],
                 error: e instanceof Error ? e : new Error(String(e))
@@ -259,43 +269,100 @@ export class UpdateService {
         const result: PostRestartResult = {
             installSuccess: true,
             installOutput: "",
+            webBuildSuccess: true,
+            webBuildOutput: "",
             migrationSuccess: true,
             migrationOutput: "",
             ranInstall: context.installDependencies,
+            ranWebBuild: context.buildWebAssets,
             ranMigrations: context.runMigrations,
             previousCommit: context.previousCommit,
             newCommit: context.newCommit
         };
 
+        // Track progress for consolidated message
+        const progress: PostRestartProgress = {
+            installDeps: context.installDependencies,
+            buildWeb: context.buildWebAssets,
+            runMigrations: context.runMigrations,
+            currentStep: "starting"
+        };
+
+        // Only send progress message if there are tasks to run
+        const hasTasks = context.installDependencies || context.buildWebAssets || context.runMigrations;
+        let progressMessage = hasTasks
+            ? await channel.send({ embeds: [getPostRestartProgressEmbed(progress)] })
+            : null;
+
+        // Helper to update progress message
+        const updateProgress = async () => {
+            if (progressMessage) {
+                await progressMessage.edit({ embeds: [getPostRestartProgressEmbed(progress)] });
+            }
+        };
+
         // 1. Install Dependencies if needed
         if (context.installDependencies) {
             try {
-                await channel.send({ embeds: [getInstallingDependenciesEmbed()] });
+                progress.currentStep = "install";
+                await updateProgress();
 
                 const { stdout: rootOutput } = await execAsync("bun install");
                 const { stdout: webOutput } = await execAsync("cd web && bun install");
 
                 result.installOutput = `📦 Root: ${rootOutput.trim() || "Done"}\n🌐 Web: ${webOutput.trim() || "Done"}`;
+                progress.installDone = true;
             } catch (err: unknown) {
                 result.installSuccess = false;
                 result.installOutput = err instanceof Error ? err.message : String(err);
+                progress.installDone = true; // Mark as done even on failure
                 console.error("Dependency Install Failed:", err);
             }
         }
 
-        // 2. Run Migrations
+        // 2. Build Web Assets if needed
+        if (context.buildWebAssets) {
+            try {
+                progress.currentStep = "build";
+                await updateProgress();
+
+                const { stdout } = await execAsync("cd web && bun run build");
+                result.webBuildOutput = stdout.trim() || "Build completed successfully";
+                progress.buildDone = true;
+            } catch (err: unknown) {
+                result.webBuildSuccess = false;
+                result.webBuildOutput = err instanceof Error ? err.message : String(err);
+                progress.buildDone = true;
+                console.error("Web Build Failed:", err);
+            }
+        }
+
+        // 3. Run Migrations
         if (context.runMigrations) {
             try {
-                await channel.send({ embeds: [getRunningMigrationsEmbed()] });
+                progress.currentStep = "migrate";
+                await updateProgress();
+
                 const { stdout } = await execAsync("bun x drizzle-kit migrate");
                 result.migrationOutput = stdout;
+                progress.migrateDone = true;
             } catch (err: unknown) {
                 result.migrationSuccess = false;
                 result.migrationOutput = err instanceof Error ? err.message : String(err);
+                progress.migrateDone = true;
                 console.error("Migration Failed:", err);
             }
         }
 
+        // Delete progress message before final result
+        if (progressMessage) {
+            try {
+                await progressMessage.delete();
+            } catch {
+                // Message may already be deleted, ignore
+            }
+        }
+
         return result;
     }