diff --git a/src/resources/extensions/gsd/db-writer.ts b/src/resources/extensions/gsd/db-writer.ts
index 2559d5e04..6963b2455 100644
--- a/src/resources/extensions/gsd/db-writer.ts
+++ b/src/resources/extensions/gsd/db-writer.ts
@@ -9,6 +9,7 @@
 // parseDecisionsTable() and parseRequirementsSections() with field fidelity.
 
 import { join, resolve } from 'node:path';
+import { readFileSync, existsSync } from 'node:fs';
 import type { Decision, Requirement } from './types.js';
 import { resolveGsdRootFile } from './paths.js';
 import { saveFile } from './files.js';
@@ -17,6 +18,58 @@ import { invalidateStateCache } from './state.js';
 import { clearPathCache } from './paths.js';
 import { clearParseCache } from './files.js';
 
+// ─── Freeform Detection ───────────────────────────────────────────────────
+
+/**
+ * Detect whether a DECISIONS.md file is in canonical table format
+ * (generated by generateDecisionsMd).
+ *
+ * Returns true only if the file starts with the canonical header
+ * ("# Decisions Register") that generateDecisionsMd produces.
+ * Files with freeform content — even if they contain an appended
+ * decisions table section — return false so the freeform content
+ * is preserved.
+ */
+export function isDecisionsTableFormat(content: string): boolean {
+  // The canonical format always starts with "# Decisions Register"
+  const firstLine = content.split('\n')[0]?.trim() ?? '';
+  if (firstLine !== '# Decisions Register') return false;
+
+  // Additionally verify the file has the canonical table header
+  return content.includes('| # | When | Scope | Decision | Choice | Rationale | Revisable?');
+}
+
+/**
+ * Generate a minimal decisions table section (header + rows) for appending
+ * to a freeform DECISIONS.md file.
+ */
+function generateDecisionsAppendBlock(decisions: Decision[]): string {
+  const lines: string[] = [];
+  lines.push('');
+  lines.push('---');
+  lines.push('');
+  lines.push('## Decisions Table');
+  lines.push('');
+  lines.push('| # | When | Scope | Decision | Choice | Rationale | Revisable? | Made By |');
+  lines.push('|---|------|-------|----------|--------|-----------|------------|---------|');
+
+  for (const d of decisions) {
+    const cells = [
+      d.id,
+      d.when_context,
+      d.scope,
+      d.decision,
+      d.choice,
+      d.rationale,
+      d.revisable,
+      d.made_by ?? 'agent',
+    ].map(cell => (cell ?? '').replace(/\|/g, '\\|'));
+    lines.push(`| ${cells.join(' | ')} |`);
+  }
+
+  return lines.join('\n') + '\n';
+}
+
 // ─── Markdown Generators ──────────────────────────────────────────────────
 
 /**
@@ -230,8 +283,31 @@ export async function saveDecisionToDb(
       }));
     }
 
-    const md = generateDecisionsMd(allDecisions);
     const filePath = resolveGsdRootFile(basePath, 'DECISIONS');
+
+    // Check if existing DECISIONS.md has freeform (non-table) content.
+    // If so, preserve that content and append/update the decisions table
+    // at the end instead of overwriting the entire file.
+    let existingContent: string | null = null;
+    if (existsSync(filePath)) {
+      existingContent = readFileSync(filePath, 'utf-8');
+    }
+
+    let md: string;
+    if (existingContent && !isDecisionsTableFormat(existingContent)) {
+      // Freeform content detected — preserve it and append decisions table.
+      // Strip any previously appended decisions table section to avoid duplication.
+      const marker = '---\n\n## Decisions Table';
+      const markerIdx = existingContent.indexOf(marker);
+      const freeformPart = markerIdx >= 0
+        ? existingContent.substring(0, markerIdx).trimEnd()
+        : existingContent.trimEnd();
+      md = freeformPart + '\n' + generateDecisionsAppendBlock(allDecisions);
+    } else {
+      // Table format or no existing file — full regeneration (original behavior)
+      md = generateDecisionsMd(allDecisions);
+    }
+
     await saveFile(filePath, md);
     // Invalidate file-read caches so deriveState() sees the updated markdown.
     // Do NOT clear the artifacts table — we just wrote to it intentionally.
diff --git a/src/resources/extensions/gsd/tests/freeform-decisions.test.ts b/src/resources/extensions/gsd/tests/freeform-decisions.test.ts
new file mode 100644
index 000000000..6a9addb44
--- /dev/null
+++ b/src/resources/extensions/gsd/tests/freeform-decisions.test.ts
@@ -0,0 +1,240 @@
+import { createTestContext } from './test-helpers.ts';
+import * as path from 'node:path';
+import * as os from 'node:os';
+import * as fs from 'node:fs';
+import {
+  openDatabase,
+  closeDatabase,
+} from '../gsd-db.ts';
+import {
+  parseDecisionsTable,
+} from '../md-importer.ts';
+import {
+  saveDecisionToDb,
+} from '../db-writer.ts';
+
+const { assertEq, assertTrue, report } = createTestContext();
+
+// ═══════════════════════════════════════════════════════════════════════════
+// Helpers
+// ═══════════════════════════════════════════════════════════════════════════
+
+function makeTmpDir(): string {
+  const dir = fs.mkdtempSync(path.join(os.tmpdir(), 'gsd-freeform-'));
+  fs.mkdirSync(path.join(dir, '.gsd'), { recursive: true });
+  return dir;
+}
+
+function cleanupDir(dir: string): void {
+  try {
+    fs.rmSync(dir, { recursive: true, force: true });
+  } catch { /* swallow */ }
+}
+
+// ═══════════════════════════════════════════════════════════════════════════
+// Bug reproduction: freeform DECISIONS.md content destroyed (#2301)
+// ═══════════════════════════════════════════════════════════════════════════
+
+console.log('\n── parseDecisionsTable silently drops freeform content ──');
+
+{
+  const freeform = `# Project Decisions
+
+## Architecture
+We decided to use a microservices architecture because monoliths don't scale.
+
+## Database
+PostgreSQL was chosen for its reliability and JSONB support.
+
+## Deployment
+- Kubernetes for orchestration
+- Helm charts for packaging
+`;
+
+  const parsed = parseDecisionsTable(freeform);
+  assertEq(parsed.length, 0, 'freeform content yields zero parsed decisions (expected — it is not a table)');
+}
+
+console.log('\n── saveDecisionToDb destroys freeform DECISIONS.md content ──');
+
+{
+  const tmpDir = makeTmpDir();
+  const dbPath = path.join(tmpDir, '.gsd', 'gsd.db');
+  const mdPath = path.join(tmpDir, '.gsd', 'DECISIONS.md');
+  openDatabase(dbPath);
+
+  const freeformContent = `# Project Decisions
+
+## Architecture
+We decided to use a microservices architecture because monoliths don't scale.
+
+## Database
+PostgreSQL was chosen for its reliability and JSONB support.
+
+## Deployment
+- Kubernetes for orchestration
+- Helm charts for packaging
+`;
+
+  // Pre-populate DECISIONS.md with freeform content
+  fs.writeFileSync(mdPath, freeformContent, 'utf-8');
+
+  try {
+    // Save a new decision — this should NOT destroy the freeform content
+    const result = await saveDecisionToDb({
+      scope: 'testing',
+      decision: 'Use Jest for unit tests',
+      choice: 'Jest',
+      rationale: 'Well-known, good DX',
+      when_context: 'M001',
+    }, tmpDir);
+
+    assertEq(result.id, 'D001', 'decision ID assigned correctly');
+
+    // Read back the file
+    const afterContent = fs.readFileSync(mdPath, 'utf-8');
+
+    // The freeform content MUST still be present
+    assertTrue(
+      afterContent.includes('microservices architecture'),
+      'freeform architecture section preserved after saveDecisionToDb',
+    );
+    assertTrue(
+      afterContent.includes('PostgreSQL was chosen'),
+      'freeform database section preserved after saveDecisionToDb',
+    );
+    assertTrue(
+      afterContent.includes('Kubernetes for orchestration'),
+      'freeform deployment section preserved after saveDecisionToDb',
+    );
+
+    // The new decision MUST also be present
+    assertTrue(
+      afterContent.includes('D001'),
+      'new decision D001 present in file',
+    );
+    assertTrue(
+      afterContent.includes('Use Jest for unit tests'),
+      'new decision text present in file',
+    );
+
+    // Save a second decision — freeform content must still survive
+    const result2 = await saveDecisionToDb({
+      scope: 'ci',
+      decision: 'Use GitHub Actions for CI',
+      choice: 'GitHub Actions',
+      rationale: 'Native integration',
+      when_context: 'M001',
+    }, tmpDir);
+
+    assertEq(result2.id, 'D002', 'second decision ID assigned correctly');
+
+    const afterContent2 = fs.readFileSync(mdPath, 'utf-8');
+
+    assertTrue(
+      afterContent2.includes('microservices architecture'),
+      'freeform content still preserved after second save',
+    );
+    assertTrue(
+      afterContent2.includes('D001'),
+      'first decision still present after second save',
+    );
+    assertTrue(
+      afterContent2.includes('D002'),
+      'second decision present after second save',
+    );
+    assertTrue(
+      afterContent2.includes('Use GitHub Actions for CI'),
+      'second decision text present in file',
+    );
+  } finally {
+    closeDatabase();
+    cleanupDir(tmpDir);
+  }
+}
+
+console.log('\n── saveDecisionToDb with table-format DECISIONS.md still regenerates normally ──');
+
+{
+  const tmpDir = makeTmpDir();
+  const dbPath = path.join(tmpDir, '.gsd', 'gsd.db');
+  const mdPath = path.join(tmpDir, '.gsd', 'DECISIONS.md');
+  openDatabase(dbPath);
+
+  // Pre-populate with canonical table format
+  const tableContent = `# Decisions Register
+
+<!-- Append-only. Never edit or remove existing rows.
+     To reverse a decision, add a new row that supersedes it.
+     Read this file at the start of any planning or research phase. -->
+
+| # | When | Scope | Decision | Choice | Rationale | Revisable? | Made By |
+|---|------|-------|----------|--------|-----------|------------|---------|
+| D001 | M001 | arch | Use REST API | REST | Simpler | Yes | human |
+`;
+
+  fs.writeFileSync(mdPath, tableContent, 'utf-8');
+
+  try {
+    const result = await saveDecisionToDb({
+      scope: 'testing',
+      decision: 'Use Vitest',
+      choice: 'Vitest',
+      rationale: 'Fast',
+      when_context: 'M001',
+    }, tmpDir);
+
+    // The pre-existing table decision was NOT in DB, so it won't appear after regen.
+    // But the new decision should be there.
+    assertEq(result.id, 'D001', 'gets D001 since DB was empty');
+
+    const afterContent = fs.readFileSync(mdPath, 'utf-8');
+    // Table-format file gets fully regenerated — this is the normal path
+    assertTrue(
+      afterContent.includes('# Decisions Register'),
+      'table-format file still has header after save',
+    );
+    assertTrue(
+      afterContent.includes('Use Vitest'),
+      'new decision present in regenerated table',
+    );
+  } finally {
+    closeDatabase();
+    cleanupDir(tmpDir);
+  }
+}
+
+console.log('\n── saveDecisionToDb with no existing DECISIONS.md creates table ──');
+
+{
+  const tmpDir = makeTmpDir();
+  const dbPath = path.join(tmpDir, '.gsd', 'gsd.db');
+  const mdPath = path.join(tmpDir, '.gsd', 'DECISIONS.md');
+  openDatabase(dbPath);
+
+  // No DECISIONS.md exists at all
+  assertTrue(!fs.existsSync(mdPath), 'DECISIONS.md does not exist initially');
+
+  try {
+    const result = await saveDecisionToDb({
+      scope: 'arch',
+      decision: 'Brand new decision',
+      choice: 'Option A',
+      rationale: 'Best fit',
+    }, tmpDir);
+
+    assertEq(result.id, 'D001', 'first decision gets D001');
+    assertTrue(fs.existsSync(mdPath), 'DECISIONS.md created');
+
+    const content = fs.readFileSync(mdPath, 'utf-8');
+    assertTrue(content.includes('# Decisions Register'), 'new file has header');
+    assertTrue(content.includes('Brand new decision'), 'new file has decision');
+  } finally {
+    closeDatabase();
+    cleanupDir(tmpDir);
+  }
+}
+
+// ═══════════════════════════════════════════════════════════════════════════
+
+report();