diff --git a/src/main/services/DocsToMarkdownConverter.ts b/src/main/services/DocsToMarkdownConverter.ts
index 910bbee..66d3e3b 100644
--- a/src/main/services/DocsToMarkdownConverter.ts
+++ b/src/main/services/DocsToMarkdownConverter.ts
@@ -23,6 +23,7 @@
  */
 
 import { delimit, escapeText } from '@shared/markdown/inlineMarks';
+import { DOCS_LINE_BREAK } from '@shared/constants';
 import { CODE_FONT_FAMILY } from './DocsDocumentBuilder';
 import type {
   GDocsApiDocument,
@@ -51,7 +52,10 @@ function readRuns(el: GDocsStructuralElement): Run[] {
     const ts = (pe.textRun?.textStyle ?? {}) as StyleBag;
     const family = (ts['weightedFontFamily'] as { fontFamily?: string } | undefined)?.fontFamily;
     runs.push({
-      text: content,
+      // A vertical tab is a line break inside the paragraph; markdown spells
+      // that as two spaces and a newline. Leaving it as a raw control
+      // character would show up as a difference on every later sync.
+      text: content.split(DOCS_LINE_BREAK).join('  \n'),
       bold: ts['bold'] === true,
       italic: ts['italic'] === true,
       strikethrough: ts['strikethrough'] === true,
diff --git a/src/main/services/MarkdownToDocsConverter.ts b/src/main/services/MarkdownToDocsConverter.ts
index ea7f142..7366074 100644
--- a/src/main/services/MarkdownToDocsConverter.ts
+++ b/src/main/services/MarkdownToDocsConverter.ts
@@ -5,6 +5,7 @@
  * to build an array of DocsElement objects suitable for the Google Docs API.
  */
 import MarkdownIt from 'markdown-it';
+import { DOCS_LINE_BREAK } from '@shared/constants';
 import type Token from 'markdown-it/lib/token.mjs';
 import type { DocsDocument, DocsElement, DocsTextRun } from '@shared/types/google-docs';
 
@@ -62,9 +63,18 @@ function parseInlineTokens(children: Token[]): DocsTextRun[] {
       case 'link_close':
         link = undefined;
         break;
+      // A newline inside a run is not a line break to Docs: insertText ends
+      // the paragraph there and starts another. Every later paragraph then
+      // fails to match its model element, so nothing is styled and the text
+      // keeps whatever it inherited. A soft-wrapped source file was enough to
+      // lose the formatting of a whole document.
       case 'softbreak':
+        // Markdown renders a wrapped line as a single space.
+        runs.push({ text: ' ' });
+        break;
       case 'hardbreak':
-        runs.push({ text: '\n' });
+        // Docs spells a within-paragraph line break as a vertical tab.
+        runs.push({ text: DOCS_LINE_BREAK });
         break;
       case 'image':
         // Inline images: use alt text from children content, src from attrs
diff --git a/src/shared/constants/index.ts b/src/shared/constants/index.ts
index 7c8d7e4..abc6960 100644
--- a/src/shared/constants/index.ts
+++ b/src/shared/constants/index.ts
@@ -66,3 +66,11 @@ export const THEMES = {
   GITHUB_LIGHT: 'github-light',
   GITHUB_DARK: 'github-dark',
 } as const;
+
+/**
+ * How Google Docs spells a line break inside a paragraph (SHIFT+ENTER).
+ *
+ * A plain newline is not one: insertText ends the paragraph there and starts
+ * another, which breaks every later paragraph's match against the model.
+ */
+export const DOCS_LINE_BREAK = '\u000b';
diff --git a/tests/unit/main/services/DocsToMarkdownConverter.test.ts b/tests/unit/main/services/DocsToMarkdownConverter.test.ts
index cffc2dd..1a968a3 100644
--- a/tests/unit/main/services/DocsToMarkdownConverter.test.ts
+++ b/tests/unit/main/services/DocsToMarkdownConverter.test.ts
@@ -250,3 +250,24 @@ describe('artefacts that make a document differ from itself', () => {
     expect(md).toContain('\\~~b');
   });
 });
+
+describe('a line break inside a paragraph', () => {
+  it('comes back as a markdown hard break, not a control character', () => {
+    // Docs spells a within-paragraph break as a vertical tab. Left raw it
+    // would read as a difference against the file on every later sync.
+    const md = convertDocsToMarkdown({
+      body: {
+        content: [
+          {
+            startIndex: 1,
+            endIndex: 26,
+            paragraph: { elements: [{ textRun: { content: 'First line.\u000bSecond line.\n' } }] },
+          },
+        ],
+      },
+    });
+
+    expect(md).not.toContain('\u000b');
+    expect(md).toContain('First line.  \nSecond line.');
+  });
+});
diff --git a/tests/unit/main/services/MarkdownToDocsConverter.test.ts b/tests/unit/main/services/MarkdownToDocsConverter.test.ts
index d0d88b1..8f0a648 100644
--- a/tests/unit/main/services/MarkdownToDocsConverter.test.ts
+++ b/tests/unit/main/services/MarkdownToDocsConverter.test.ts
@@ -1,5 +1,6 @@
 import { describe, it, expect } from 'vitest';
 import { convertMarkdownToDocs } from '@main/services/MarkdownToDocsConverter';
+import { flattenElements, getLeafText } from '@main/services/DocsDocumentBuilder';
 
 describe('MarkdownToDocsConverter', () => {
   it('should convert a plain paragraph', () => {
@@ -171,3 +172,40 @@ describe('a table written directly under the line above it', () => {
     expect(doc.elements.map((e) => e.type)).toEqual(['list_item']);
   });
 });
+
+describe('line breaks inside a paragraph', () => {
+  // A newline in a run's text is not a line break to Docs -- insertText splits
+  // it into a whole new paragraph. Every later paragraph then fails to match
+  // its model element, so nothing gets styled and the inserted text keeps
+  // whatever heading style it inherited. A soft-wrapped source file was enough
+  // to lose the formatting of an entire document.
+  const leafText = (md: string): string[] =>
+    flattenElements(convertMarkdownToDocs(md).elements).map((e) => getLeafText(e));
+
+  it('joins a soft-wrapped line with a space, as markdown renders it', () => {
+    expect(leafText('Scaffolds the thing if absent,\nthen reloads Caddy.\n')).toEqual([
+      'Scaffolds the thing if absent, then reloads Caddy.',
+    ]);
+  });
+
+  it('keeps a hard break inside the paragraph, as Docs spells it', () => {
+    // Docs writes a within-paragraph line break as a vertical tab.
+    expect(leafText('First line.  \nSecond line.\n')).toEqual([
+      'First line.\u000bSecond line.',
+    ]);
+  });
+
+  it('never leaves a newline in an inline element', () => {
+    const md = [
+      '# A heading that\nwraps',
+      '',
+      '- a list item that\n  wraps too',
+      '',
+      'Body text that\nwraps as well.',
+    ].join('\n');
+
+    for (const text of leafText(md)) {
+      expect(text).not.toContain('\n');
+    }
+  });
+});