diff --git a/src/services/sqlite/SessionStore.ts b/src/services/sqlite/SessionStore.ts
index aaaf8754..110990f7 100644
--- a/src/services/sqlite/SessionStore.ts
+++ b/src/services/sqlite/SessionStore.ts
@@ -14,6 +14,7 @@ import {
 } from '../../types/database.js';
 import type { PendingMessageStore } from './PendingMessageStore.js';
 import { computeObservationContentHash, findDuplicateObservation } from './observations/store.js';
+import { parseFileList } from './observations/files.js';
 
 /**
  * Session data store for SDK sessions, observations, and summaries
@@ -1309,20 +1310,10 @@ export class SessionStore {
 
     for (const row of rows) {
       // Parse files_read
-      if (row.files_read) {
-        const files = JSON.parse(row.files_read);
-        if (Array.isArray(files)) {
-          files.forEach(f => filesReadSet.add(f));
-        }
-      }
+      parseFileList(row.files_read).forEach(f => filesReadSet.add(f));
 
       // Parse files_modified
-      if (row.files_modified) {
-        const files = JSON.parse(row.files_modified);
-        if (Array.isArray(files)) {
-          files.forEach(f => filesModifiedSet.add(f));
-        }
-      }
+      parseFileList(row.files_modified).forEach(f => filesModifiedSet.add(f));
     }
 
     return {
diff --git a/src/services/sqlite/observations/files.ts b/src/services/sqlite/observations/files.ts
index e9bcba28..ec122fd3 100644
--- a/src/services/sqlite/observations/files.ts
+++ b/src/services/sqlite/observations/files.ts
@@ -7,6 +7,21 @@ import { Database } from 'bun:sqlite';
 import { logger } from '../../../utils/logger.js';
 import type { SessionFilesResult } from './types.js';
 
+/**
+ * Safely parse a JSON array string from the DB.
+ * Handles legacy bare-path strings (e.g. "/foo/bar.ts") by wrapping them
+ * in an array instead of crashing with a SyntaxError (fix for #1359).
+ */
+export function parseFileList(value: string | null | undefined): string[] {
+  if (!value) return [];
+  try {
+    const parsed = JSON.parse(value);
+    return Array.isArray(parsed) ? parsed : [String(parsed)];
+  } catch {
+    return [value];
+  }
+}
+
 /**
  * Get aggregated files from all observations for a session
  */
@@ -30,20 +45,10 @@ export function getFilesForSession(
 
   for (const row of rows) {
     // Parse files_read
-    if (row.files_read) {
-      const files = JSON.parse(row.files_read);
-      if (Array.isArray(files)) {
-        files.forEach(f => filesReadSet.add(f));
-      }
-    }
+    parseFileList(row.files_read).forEach(f => filesReadSet.add(f));
 
     // Parse files_modified
-    if (row.files_modified) {
-      const files = JSON.parse(row.files_modified);
-      if (Array.isArray(files)) {
-        files.forEach(f => filesModifiedSet.add(f));
-      }
-    }
+    parseFileList(row.files_modified).forEach(f => filesModifiedSet.add(f));
   }
 
   return {
diff --git a/src/services/sync/ChromaSync.ts b/src/services/sync/ChromaSync.ts
index 9f3e01d1..ecf208e1 100644
--- a/src/services/sync/ChromaSync.ts
+++ b/src/services/sync/ChromaSync.ts
@@ -16,6 +16,7 @@ import { ChromaMcpManager } from './ChromaMcpManager.js';
 import { ParsedObservation, ParsedSummary } from '../../sdk/parser.js';
 import { SessionStore } from '../sqlite/SessionStore.js';
 import { logger } from '../../utils/logger.js';
+import { parseFileList } from '../sqlite/observations/files.js';
 
 interface ChromaDocument {
   id: string;
@@ -125,8 +126,8 @@ export class ChromaSync {
     // Parse JSON fields
     const facts = obs.facts ? JSON.parse(obs.facts) : [];
     const concepts = obs.concepts ? JSON.parse(obs.concepts) : [];
-    const files_read = obs.files_read ? JSON.parse(obs.files_read) : [];
-    const files_modified = obs.files_modified ? JSON.parse(obs.files_modified) : [];
+    const files_read = parseFileList(obs.files_read);
+    const files_modified = parseFileList(obs.files_modified);
 
     const baseMetadata: Record<string, string | number> = {
       sqlite_id: obs.id,
diff --git a/tests/services/sqlite/parse-file-list.test.ts b/tests/services/sqlite/parse-file-list.test.ts
new file mode 100644
index 00000000..e4ee55fb
--- /dev/null
+++ b/tests/services/sqlite/parse-file-list.test.ts
@@ -0,0 +1,46 @@
+/**
+ * Tests for parseFileList (fix for #1359)
+ *
+ * Validates safe JSON array parsing for files_read/files_modified DB columns
+ * that may contain legacy bare path strings instead of JSON arrays.
+ */
+import { describe, it, expect } from 'bun:test';
+import { parseFileList } from '../../../src/services/sqlite/observations/files.js';
+
+describe('parseFileList', () => {
+  it('returns [] for null', () => {
+    expect(parseFileList(null)).toEqual([]);
+  });
+
+  it('returns [] for undefined', () => {
+    expect(parseFileList(undefined)).toEqual([]);
+  });
+
+  it('returns [] for empty string', () => {
+    expect(parseFileList('')).toEqual([]);
+  });
+
+  it('returns [] for empty JSON array', () => {
+    expect(parseFileList('[]')).toEqual([]);
+  });
+
+  it('parses a normal JSON array', () => {
+    expect(parseFileList('["/a/b.ts","/c/d.ts"]')).toEqual(['/a/b.ts', '/c/d.ts']);
+  });
+
+  it('wraps a bare path in an array instead of crashing', () => {
+    expect(parseFileList('/Users/foo/bar.go')).toEqual(['/Users/foo/bar.go']);
+  });
+
+  it('wraps a Windows bare path in an array', () => {
+    expect(parseFileList('C:\\Users\\foo\\bar.ts')).toEqual(['C:\\Users\\foo\\bar.ts']);
+  });
+
+  it('handles invalid JSON by treating value as single element', () => {
+    expect(parseFileList('not valid json {')).toEqual(['not valid json {']);
+  });
+
+  it('wraps a JSON scalar string in an array', () => {
+    expect(parseFileList('"single-file.ts"')).toEqual(['single-file.ts']);
+  });
+});