diff --git a/package-lock.json b/package-lock.json
index 44854e0d..04909dc4 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -47,6 +47,7 @@
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@@ -82,6 +83,20 @@
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+      "license": "MIT",
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@@ -276,6 +291,121 @@
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@@ -4361,6 +4501,19 @@
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@@ -4579,6 +4754,57 @@
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+      "license": "BSD-2-Clause",
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+      "dev": true,
+      "license": "BSD-3-Clause",
+      "dependencies": {
+        "psl": "^1.1.33",
+        "punycode": "^2.1.1",
+        "universalify": "^0.2.0",
+        "url-parse": "^1.5.3"
+      },
+      "engines": {
+        "node": ">=6"
+      }
+    },
+    "node_modules/tough-cookie/node_modules/universalify": {
+      "version": "0.2.0",
+      "resolved": "https://registry.npmjs.org/universalify/-/universalify-0.2.0.tgz",
+      "integrity": "sha512-CJ1QgKmNg3CwvAv/kOFmtnEN05f0D/cn9QntgNOQlQF9dgvVTHj3t+8JPdjqawCHk7V/KA+fbUqzZ9XWhcqPUg==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">= 4.0.0"
+      }
+    },
     "node_modules/tr46": {
       "version": "0.0.3",
       "resolved": "https://registry.npmjs.org/tr46/-/tr46-0.0.3.tgz",
@@ -11430,6 +11943,7 @@
       "resolved": "https://registry.npmjs.org/type-is/-/type-is-1.6.18.tgz",
       "integrity": "sha512-TkRKr9sUTxEH8MdfuCSP7VizJyzRNMjj2J2do2Jr3Kym598JVdEksuzPQCnlFPW4ky9Q+iA+ma9BGm06XQBy8g==",
       "license": "MIT",
+      "peer": true,
       "dependencies": {
         "media-typer": "0.3.0",
         "mime-types": "~2.1.24"
@@ -11465,7 +11979,6 @@
       "integrity": "sha512-jl1vZzPDinLr9eUt3J/t7V6FgNEw9QjvBPdysz9KfQDD41fQrC2Y4vKQdiaUpFT4bXlb1RHhLpp8wtm6M5TgSw==",
       "devOptional": true,
       "license": "Apache-2.0",
-      "peer": true,
       "bin": {
         "tsc": "bin/tsc",
         "tsserver": "bin/tsserver"
@@ -11622,6 +12135,17 @@
         "browserslist": ">= 4.21.0"
       }
     },
+    "node_modules/url-parse": {
+      "version": "1.5.10",
+      "resolved": "https://registry.npmjs.org/url-parse/-/url-parse-1.5.10.tgz",
+      "integrity": "sha512-WypcfiRhfeUP9vvF0j6rw0J3hrWrw6iZv3+22h6iRMJ/8z1Tj6XfLP4DsUix5MhMPnXpiHDoKyoZ/bdCkwBCiQ==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "querystringify": "^2.1.1",
+        "requires-port": "^1.0.0"
+      }
+    },
     "node_modules/url-parse-lax": {
       "version": "3.0.0",
       "resolved": "https://registry.npmjs.org/url-parse-lax/-/url-parse-lax-3.0.0.tgz",
@@ -11656,6 +12180,7 @@
       "resolved": "https://registry.npmjs.org/utils-merge/-/utils-merge-1.0.1.tgz",
       "integrity": "sha512-pMZTvIkT1d+TFGvDOqodOclx0QWkkgi6Tdoa8gC8ffGAAqz9pzPTZWAybbsHHoED/ztMtkv/VoYTYyShUn81hA==",
       "license": "MIT",
+      "peer": true,
       "engines": {
         "node": ">= 0.4.0"
       }
@@ -11691,6 +12216,19 @@
       "integrity": "sha512-dpojBhNsCNN7T82Tm7k26A6G9ML3NkhDsnw9n/eoxSRlVBB4CEtIQ/KTCLI2Fwf3ataSXRhYFkQi3SlnFwPvPQ==",
       "license": "MIT"
     },
+    "node_modules/w3c-xmlserializer": {
+      "version": "5.0.0",
+      "resolved": "https://registry.npmjs.org/w3c-xmlserializer/-/w3c-xmlserializer-5.0.0.tgz",
+      "integrity": "sha512-o8qghlI8NZHU1lLPrpi2+Uq7abh4GGPpYANlalzWxyWteJOCsr/P+oPBA49TOLu5FTZO4d3F9MnWJfiMo4BkmA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "xml-name-validator": "^5.0.0"
+      },
+      "engines": {
+        "node": ">=18"
+      }
+    },
     "node_modules/watchpack": {
       "version": "2.5.0",
       "resolved": "https://registry.npmjs.org/watchpack/-/watchpack-2.5.0.tgz",
@@ -11733,7 +12271,6 @@
       "integrity": "sha512-Qphch25abbMNtekmEGJmeRUhLDbe+QfiWTiqpKYkpCOWY64v9eyl+KRRLmqOFA2AvKPpc9DC6+u2n76tQLBoaA==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@types/eslint-scope": "^3.7.7",
         "@types/estree": "^1.0.8",
@@ -11783,7 +12320,6 @@
       "integrity": "sha512-MfwFQ6SfwinsUVi0rNJm7rHZ31GyTcpVE5pgVA3hwFRb7COD4TzjUUwhGWKfO50+xdc2MQPuEBBJoqIMGt3JDw==",
       "dev": true,
       "license": "MIT",
-      "peer": true,
       "dependencies": {
         "@discoveryjs/json-ext": "^0.6.1",
         "@webpack-cli/configtest": "^3.0.1",
@@ -11898,6 +12434,43 @@
         "node": ">=10.13.0"
       }
     },
+    "node_modules/whatwg-encoding": {
+      "version": "3.1.1",
+      "resolved": "https://registry.npmjs.org/whatwg-encoding/-/whatwg-encoding-3.1.1.tgz",
+      "integrity": "sha512-6qN4hJdMwfYBtE3YBTTHhoeuUrDBPZmbQaxWAqSALV/MeEnR5z1xd8UKud2RAkFoPkmB+hli1TZSnyi84xz1vQ==",
+      "deprecated": "Use @exodus/bytes instead for a more spec-conformant and faster implementation",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "iconv-lite": "0.6.3"
+      },
+      "engines": {
+        "node": ">=18"
+      }
+    },
+    "node_modules/whatwg-encoding/node_modules/iconv-lite": {
+      "version": "0.6.3",
+      "resolved": "https://registry.npmjs.org/iconv-lite/-/iconv-lite-0.6.3.tgz",
+      "integrity": "sha512-4fCk79wshMdzMp2rH06qWrJE4iolqLhCUH+OiuIgU++RB0+94NlDL81atO7GX55uUKueo0txHNtvEyI6D7WdMw==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "safer-buffer": ">= 2.1.2 < 3.0.0"
+      },
+      "engines": {
+        "node": ">=0.10.0"
+      }
+    },
+    "node_modules/whatwg-mimetype": {
+      "version": "4.0.0",
+      "resolved": "https://registry.npmjs.org/whatwg-mimetype/-/whatwg-mimetype-4.0.0.tgz",
+      "integrity": "sha512-QaKxh0eNIi2mE9p2vEdzfagOKHCcj1pJ56EEHGQOVxp8r9/iszLUUV7v89x9O1p/T+NlTM5W7jW6+cz4Fq1YVg==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=18"
+      }
+    },
     "node_modules/whatwg-url": {
       "version": "5.0.0",
       "resolved": "https://registry.npmjs.org/whatwg-url/-/whatwg-url-5.0.0.tgz",
@@ -12101,6 +12674,16 @@
         "url": "https://github.com/sponsors/sindresorhus"
       }
     },
+    "node_modules/xml-name-validator": {
+      "version": "5.0.0",
+      "resolved": "https://registry.npmjs.org/xml-name-validator/-/xml-name-validator-5.0.0.tgz",
+      "integrity": "sha512-EvGK8EJ3DhaHfbRlETOWAS5pO9MZITeauHKJyb8wyajUfQUenkIg2MvLDTZ4T/TgIcm3HU0TFBgWWboAZ30UHg==",
+      "dev": true,
+      "license": "Apache-2.0",
+      "engines": {
+        "node": ">=18"
+      }
+    },
     "node_modules/xmlchars": {
       "version": "2.2.0",
       "resolved": "https://registry.npmjs.org/xmlchars/-/xmlchars-2.2.0.tgz",
@@ -12296,7 +12879,6 @@
       "resolved": "https://registry.npmjs.org/zod/-/zod-3.25.76.tgz",
       "integrity": "sha512-gzUt/qt81nXsFGKIFcC3YnfEAx5NkunCfnDlvuBSSFS02bcXu4Lmea0AFIUwbLWxWPx3d9p8S5QoaujKcNQxcQ==",
       "license": "MIT",
-      "peer": true,
       "funding": {
         "url": "https://github.com/sponsors/colinhacks"
       }
diff --git a/package.json b/package.json
index e4e8bd73..6b29b278 100644
--- a/package.json
+++ b/package.json
@@ -120,6 +120,7 @@
     "commander": "^13.1.0",
     "esbuild": "^0.27.2",
     "js-tiktoken": "^1.0.21",
+    "jsdom": "^24.1.3",
     "nexe": "^5.0.0-beta.4",
     "nodemon": "^3.0.2",
     "shx": "^0.3.4",
diff --git a/test/test-markdown-editor-roundtrip.js b/test/test-markdown-editor-roundtrip.js
new file mode 100644
index 00000000..a8ed5ddc
--- /dev/null
+++ b/test/test-markdown-editor-roundtrip.js
@@ -0,0 +1,270 @@
+/**
+ * Regression test for #437/#440: markdown editor round-trip stability.
+ *
+ * Originally written against the Tiptap+tiptap-markdown editor (0.2.39) which
+ * round-tripped raw markdown through a ProseMirror document model and lost
+ * structure on save. PR #442 replaces that editor with a source-backed
+ * CodeMirror editor where getValue() === setValue input.
+ *
+ * This test mounts the actual mountMarkdownEditor exported by
+ * src/ui/file-preview/src/markdown/editor.ts (built in dist/) and asserts that
+ * for every fixture from #437 / #440 / #97 / a live in-the-wild corruption,
+ * editor.getValue() === input.
+ *
+ * Pre-#442: every case fails (Tiptap drift writes corruptions back via
+ * autosave).
+ * Post-#442: every case must pass (raw markdown is canonical, no
+ * parse-and-reserialize step exists).
+ */
+
+import assert from 'assert';
+import { JSDOM } from 'jsdom';
+
+// Bootstrap a DOM that CodeMirror can mount into. Must run before importing.
+const dom = new JSDOM('<!doctype html><html><body><div id="root"></div></body></html>', {
+  pretendToBeVisual: true,
+});
+globalThis.window = dom.window;
+globalThis.document = dom.window.document;
+globalThis.HTMLElement = dom.window.HTMLElement;
+globalThis.HTMLTextAreaElement = dom.window.HTMLTextAreaElement;
+globalThis.HTMLInputElement = dom.window.HTMLInputElement;
+globalThis.HTMLButtonElement = dom.window.HTMLButtonElement;
+globalThis.HTMLSelectElement = dom.window.HTMLSelectElement;
+globalThis.Node = dom.window.Node;
+globalThis.Range = dom.window.Range;
+globalThis.DOMParser = dom.window.DOMParser;
+globalThis.getComputedStyle = dom.window.getComputedStyle;
+globalThis.MutationObserver = dom.window.MutationObserver;
+globalThis.requestAnimationFrame = (cb) => setTimeout(cb, 0);
+globalThis.cancelAnimationFrame = (id) => clearTimeout(id);
+
+const { mountMarkdownEditor, renderMarkdownEditorShell } = await import(
+  '../dist/ui/file-preview/src/markdown/editor.js'
+);
+
+function mountFor(value, view = 'markdown') {
+  const root = document.getElementById('root');
+  root.innerHTML = renderMarkdownEditorShell({ view });
+  const target = root.querySelector('#markdown-editor-root');
+  return mountMarkdownEditor({
+    target,
+    value,
+    view,
+    currentFilePath: '/tmp/test.md',
+    onChange: () => {},
+  });
+}
+
+function roundTrip(input, view = 'markdown') {
+  const editor = mountFor(input, view);
+  const out = editor.getValue();
+  editor.destroy();
+  return out;
+}
+
+// ---------------------------------------------------------------------------
+// Fixtures: every case that was failing on the Tiptap implementation.
+// ---------------------------------------------------------------------------
+
+async function testPipeTableSurvivesRoundTrip() {
+  const input = '# Test\n\n| A | B |\n|---|---|\n| 1 | 2 |\n';
+  const output = roundTrip(input);
+  assert.strictEqual(output, input, 'pipe table must not collapse to "AB12"');
+}
+
+async function testTildeIsNotEscaped() {
+  const input = 'Use ~ to negate.\n';
+  const output = roundTrip(input);
+  assert.strictEqual(output, input, 'tilde must not gain a backslash escape');
+}
+
+async function testAdjacentHeadingsKeepOriginalSpacing() {
+  const input = '### Heading One\nBody.\n### Heading Two\nMore.\n';
+  const output = roundTrip(input);
+  assert.strictEqual(output, input, 'block spacing must be preserved');
+}
+
+async function testWikilinkSurvivesRoundTrip() {
+  const input = '# Test\nSee [[Other Note]].\n';
+  const output = roundTrip(input);
+  assert.strictEqual(output, input, 'wikilink + heading must round-trip identically');
+}
+
+async function testTrailingNewlineSurvives() {
+  const input = 'A single paragraph.\n';
+  const output = roundTrip(input);
+  assert.strictEqual(output, input, 'trailing newline must not be stripped');
+}
+
+async function testCombinedBugReportFile() {
+  const input = '# Test\nSee [[Other Note]].\n\n| A | B |\n|---|---|\n| 1 | 2 |\n';
+  const output = roundTrip(input);
+  assert.strictEqual(output, input, '#437 combined fixture must not drift');
+}
+
+async function testYamlFrontmatterSurvives() {
+  const input = '---\ntitle: My Note\ntags: [a, b]\ndescription: A test file\n---\n\n# Body\n\nContent here.\n';
+  const output = roundTrip(input);
+  assert.strictEqual(output, input, 'YAML frontmatter must not be parsed as Setext heading');
+}
+
+async function testSquareBracketsNotEscaped() {
+  const input = '- [x] task done\n- [ ] task todo\n';
+  const output = roundTrip(input);
+  assert.strictEqual(output, input, 'GFM task list brackets must not be escaped');
+}
+
+async function testUnderscoresNotEscaped() {
+  const input = 'Use the my_variable_name in code, plus snake_case_func().\n';
+  const output = roundTrip(input);
+  assert.strictEqual(output, input, 'underscores in identifiers must not be escaped');
+}
+
+async function testTildePathNotEscaped() {
+  const input = 'Open ~/Documents/notes.md to continue.\n';
+  const output = roundTrip(input);
+  assert.strictEqual(output, input, '~/path must not be escaped');
+}
+
+async function testLooseListPreserved() {
+  const input = '- first item\n\n- second item\n\n- third item\n';
+  const output = roundTrip(input);
+  assert.strictEqual(output, input, 'loose-list blank lines must not be stripped');
+}
+
+async function testCrlfDocumentedBehaviour() {
+  // CodeMirror's EditorState normalizes line endings to LF internally by
+  // default — getValue() returns LF only. In practice the file-preview UI
+  // is seeded from read_file's text response, which is already LF-normalized
+  // upstream by TextFileHandler (PR #438 fixes that path), so this case
+  // never fires through the normal flow.
+  //
+  // We document the behaviour here so that, if anyone wires up direct CRLF
+  // input later (e.g. raw-mode preview of a Windows file), they know to
+  // configure EditorState with an explicit lineSeparator and write-side
+  // CRLF preservation.
+  const input = '# Heading\r\nFirst line.\r\nSecond line.\r\n';
+  const output = roundTrip(input);
+  if (output === input) {
+    return; // Future-proof: passes if CRLF support is added.
+  }
+  // Tolerate the LF-normalization but assert it is ONLY that — not the
+  // structural drift the Tiptap pipeline used to introduce.
+  const normalizedExpected = input.replace(/\r\n/g, '\n');
+  assert.strictEqual(
+    output,
+    normalizedExpected,
+    'CRLF normalization is permitted; structural drift is not'
+  );
+}
+
+async function testReadmeStyleFileNotCollapsed() {
+  // Mirrors a real corruption captured live: a 200+ line README with mixed
+  // markdown was reduced to ~22 lines after a single edit_block call.
+  const input = [
+    '# My Project',
+    '',
+    'A short intro paragraph explaining what the project does.',
+    '',
+    '## Installation',
+    '',
+    '```bash',
+    'npm install my-project',
+    '```',
+    '',
+    '## Configuration',
+    '',
+    '| Variable | Default | Description |',
+    '|---|---|---|',
+    '| FOO | `bar` | The foo setting |',
+    '| BAZ | `qux` | The baz setting |',
+    '',
+    '## Usage',
+    '',
+    '- First, run `npm start`',
+    '- Then, open `http://localhost:3000`',
+    '- Finally, press `Ctrl+C` to stop',
+    '',
+    'See [the docs](https://example.com) for more.',
+    '',
+  ].join('\n');
+  const output = roundTrip(input);
+  const inputLines = input.split('\n').length;
+  const outputLines = output.split('\n').length;
+  if (outputLines / inputLines < 0.5) {
+    throw new Error(
+      `output collapsed from ${inputLines} to ${outputLines} lines. The >70% threshold ` +
+      `in computeEditBlocks would emit a single edit_block replacing the entire file.`
+    );
+  }
+  assert.strictEqual(output, input, 'README-style file must round-trip unchanged');
+}
+
+async function testTableInsideRealisticDoc() {
+  const input = [
+    '# Section A',
+    '',
+    'Prose paragraph one with content.',
+    'A second line of prose.',
+    '',
+    '## Comparison',
+    '',
+    '| Feature | A | B |',
+    '|---|---|---|',
+    '| Speed | fast | slow |',
+    '| Cost | low | high |',
+    '| Quality | good | bad |',
+    '',
+    '## Section B',
+    '',
+    'More prose after the table that must not be deleted.',
+    'Final line of the document.',
+    '',
+  ].join('\n');
+  const output = roundTrip(input);
+  if (!output.includes('Section A') || !output.includes('Section B') ||
+      !output.includes('Final line of the document') ||
+      !output.includes('Prose paragraph one')) {
+    throw new Error('lost prose around the table:\n' + output);
+  }
+  assert.strictEqual(output, input, 'realistic doc with embedded table must round-trip unchanged');
+}
+
+async function runAllTests() {
+  const tests = [
+    testPipeTableSurvivesRoundTrip,
+    testTildeIsNotEscaped,
+    testAdjacentHeadingsKeepOriginalSpacing,
+    testWikilinkSurvivesRoundTrip,
+    testTrailingNewlineSurvives,
+    testCombinedBugReportFile,
+    testYamlFrontmatterSurvives,
+    testSquareBracketsNotEscaped,
+    testUnderscoresNotEscaped,
+    testTildePathNotEscaped,
+    testLooseListPreserved,
+    testCrlfDocumentedBehaviour,
+    testReadmeStyleFileNotCollapsed,
+    testTableInsideRealisticDoc,
+  ];
+  let passed = 0;
+  let failed = 0;
+  for (const t of tests) {
+    try {
+      await t();
+      passed++;
+      console.log(`OK   ${t.name}`);
+    } catch (err) {
+      failed++;
+      console.error(`FAIL ${t.name}`);
+      console.error(`     ${err.message}`);
+    }
+  }
+  console.log(`\n${passed} passed, ${failed} failed (of ${tests.length})`);
+  if (failed > 0) {
+    process.exit(1);
+  }
+}
+
+runAllTests();