@@ -60,6 +60,9 @@ jobs:
           EOF
           npm run build  # This includes CSS building via npm run build-css
 
+      - name: Check Obsidian Sync bundle size budget
+        run: npm run check:bundle-size
+
       - name: Verify release notes
         run: |
           if [ ! -f "$RELEASE_NOTES_PATH" ]; then
 
@@ -7,6 +7,34 @@ on:
     branches: [ main, develop, v3-maintenance ]
 
 jobs:
+  bundle-size:
+    runs-on: ubuntu-latest
+    steps:
+    - name: Checkout code
+      uses: actions/checkout@v4
+      with:
+        submodules: true
+
+    - name: Setup Node.js
+      uses: actions/setup-node@v4
+      with:
+        node-version: '20'
+        cache: 'npm'
+
+    - name: Install dependencies
+      run: npm ci --prefer-offline --no-audit
+      timeout-minutes: 5
+
+    - name: Test bundle size guard
+      run: node --test scripts/check-bundle-size.test.mjs
+
+    - name: Build production plugin
+      run: npm run build
+      timeout-minutes: 10
+
+    - name: Check Obsidian Sync bundle size budget
+      run: npm run check:bundle-size
+
   test:
     runs-on: ubuntu-latest
     strategy:
 
@@ -34,6 +34,8 @@ When a change has user-facing documentation, include a canonical tasknotes.dev l
 
 ## Fixed
 
+- (#2336) Reduced the plugin bundle below Obsidian Sync Standard's 5 MB per-file limit so it can sync between devices again. Thanks to @kmalakoff for reporting and @CyberBlaed for confirming.
+
 - (#2301) Fixed clicking the Pomodoro timer display to edit its duration. Thanks to @minnyee for reporting and identifying the cause.
 
 - (#2328) Fixed direct status edits on occurrence notes not updating the recurring parent’s completion history or creating the next occurrence when configured. Thanks to @mudnug for reporting this.
@@ -96,6 +96,8 @@ const context = await esbuild.context({
 	treeShaking: true,
 	outfile: "main.js",
 	minify: prod,
+	// Avoid bulky Unicode escapes in translations; keep the bundle within Obsidian Sync's limit.
+	charset: "utf8",
 	plugins: [markdownPlugin, ...(!prod ? [copyToVaultPlugin] : [])],
 });
 
 
@@ -7,6 +7,7 @@
 		"build": "npm run build-css && node generate-release-notes-import.mjs && tsc -noEmit --skipLibCheck && node esbuild.config.mjs production",
 		"dev": "npm run build-css && node generate-release-notes-import.mjs && node esbuild.config.mjs",
 		"build:test": "npm run build && node copy-files.mjs",
+		"check:bundle-size": "node scripts/check-bundle-size.mjs",
 		"copy-files": "node copy-files.mjs",
 		"build-css": "node build-css.mjs",
 		"e2e": "playwright test",
 
@@ -0,0 +1,20 @@
+import { statSync } from "node:fs";
+
+// Use decimal MB conservatively, and require headroom below the limit.
+const limit = 5_000_000;
+const bundle = process.argv[2] ?? "main.js";
+
+try {
+	const stats = statSync(bundle);
+	if (!stats.isFile() || stats.size === 0) {
+		throw new Error("expected a non-empty bundle file");
+	}
+	console.log(`${bundle}: ${stats.size.toLocaleString("en-US")} bytes; must be below ${limit.toLocaleString("en-US")} bytes.`);
+	if (stats.size >= limit) {
+		console.error("Bundle exceeds the size budget for Obsidian Sync Standard. Reduce the production bundle before releasing.");
+		process.exitCode = 1;
+	}
+} catch (error) {
+	console.error(`Cannot check bundle ${bundle}: ${error.message}`);
+	process.exitCode = 1;
+}
@@ -0,0 +1,38 @@
+import { test } from "node:test";
+import assert from "node:assert/strict";
+import { mkdtempSync, writeFileSync, truncateSync, rmSync } from "node:fs";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { fileURLToPath } from "node:url";
+import { spawnSync } from "node:child_process";
+
+const script = fileURLToPath(new URL("./check-bundle-size.mjs", import.meta.url));
+
+for (const [name, size, expectedStatus] of [
+	["below limit", 4_999_999, 0],
+	["at limit", 5_000_000, 1],
+	["above limit", 5_000_001, 1],
+	["empty file", 0, 1],
+	["missing file", null, 1],
+]) {
+	test(name, () => {
+		const directory = mkdtempSync(join(tmpdir(), "tasknotes-bundle-size-"));
+		try {
+			const bundle = join(directory, "main.js");
+			if (size !== null) {
+				writeFileSync(bundle, "");
+				truncateSync(bundle, size);
+			}
+			// Check both the default main.js path and an explicit path.
+			for (const args of [[], [bundle]]) {
+				const result = spawnSync(process.execPath, [script, ...args], {
+					cwd: directory,
+					encoding: "utf8",
+				});
+				assert.equal(result.status, expectedStatus, result.stdout + result.stderr);
+			}
+		} finally {
+			rmSync(directory, { recursive: true, force: true });
+		}
+	});
+}