diff --git a/get-shit-done/bin/lib/configuration.generated.cjs b/get-shit-done/bin/lib/configuration.generated.cjs
index 0903ce74e..fa3c50748 100644
--- a/get-shit-done/bin/lib/configuration.generated.cjs
+++ b/get-shit-done/bin/lib/configuration.generated.cjs
@@ -21,7 +21,16 @@ const CONFIG_DEFAULTS = require('../../../sdk/shared/config-defaults.manifest.js
 const SCHEMA_MANIFEST = require('../../../sdk/shared/config-schema.manifest.json');
 const VALID_CONFIG_KEYS = new Set(SCHEMA_MANIFEST.validKeys);
 const RUNTIME_STATE_KEYS = new Set(SCHEMA_MANIFEST.runtimeStateKeys);
-const DYNAMIC_KEY_PATTERNS = SCHEMA_MANIFEST.dynamicKeyPatterns.map(p => ({ ...p, test: (key) => new RegExp(p.source).test(key) }));
+const DYNAMIC_KEY_PATTERNS = SCHEMA_MANIFEST.dynamicKeyPatterns.map((p) => {
+  const pattern = new RegExp(p.source);
+  return {
+    ...p,
+    test: (key) => {
+      pattern.lastIndex = 0;
+      return pattern.test(key);
+    },
+  };
+});
 
 // ─── Depth → Granularity mapping ─────────────────────────────────────────────
 const DEPTH_TO_GRANULARITY = {
@@ -201,7 +210,13 @@ async function migrateOnDisk(cwd, workstream) {
             }
         }
     }
-    writeFileSync(configPath, JSON.stringify(result, null, 2));
+    try {
+        writeFileSync(configPath, JSON.stringify(result, null, 2));
+    }
+    catch (err) {
+        const msg = err instanceof Error ? err.message : String(err);
+        throw new Error(`Failed to write migrated config at ${configPath}: ${msg}`);
+    }
     return { migrated: true, normalizations, wrote: configPath };
 }
 
diff --git a/sdk/scripts/gen-configuration.mjs b/sdk/scripts/gen-configuration.mjs
index 41679462a..3a474b6ef 100644
--- a/sdk/scripts/gen-configuration.mjs
+++ b/sdk/scripts/gen-configuration.mjs
@@ -12,7 +12,7 @@
  * Or from repo root: node sdk/scripts/gen-configuration.mjs
  */
 
-import { readFileSync, writeFileSync } from 'node:fs';
+import { existsSync, readFileSync, writeFileSync } from 'node:fs';
 import { fileURLToPath } from 'node:url';
 import { resolve, dirname } from 'node:path';
 
@@ -21,10 +21,13 @@ const repoRoot = resolve(here, '..', '..');
 
 // ─── Read the compiled dist file for function extraction ─────────────────────
 
-const distSrc = readFileSync(
-  resolve(here, '..', 'dist', 'configuration', 'index.js'),
-  'utf-8',
-);
+const distPath = resolve(here, '..', 'dist', 'configuration', 'index.js');
+if (!existsSync(distPath)) {
+  throw new Error(
+    `Missing compiled configuration module at ${distPath}. Run "cd sdk && npm run build" first.`,
+  );
+}
+const distSrc = readFileSync(distPath, 'utf-8');
 
 /**
  * Extract a named function from the compiled dist source by scanning for
@@ -102,7 +105,16 @@ export function buildConfigurationCjs() {
     `const SCHEMA_MANIFEST = require('../../../sdk/shared/config-schema.manifest.json');`,
     `const VALID_CONFIG_KEYS = new Set(SCHEMA_MANIFEST.validKeys);`,
     `const RUNTIME_STATE_KEYS = new Set(SCHEMA_MANIFEST.runtimeStateKeys);`,
-    `const DYNAMIC_KEY_PATTERNS = SCHEMA_MANIFEST.dynamicKeyPatterns.map(p => ({ ...p, test: (key) => new RegExp(p.source).test(key) }));`,
+    `const DYNAMIC_KEY_PATTERNS = SCHEMA_MANIFEST.dynamicKeyPatterns.map((p) => {`,
+    `  const pattern = new RegExp(p.source);`,
+    `  return {`,
+    `    ...p,`,
+    `    test: (key) => {`,
+    `      pattern.lastIndex = 0;`,
+    `      return pattern.test(key);`,
+    `    },`,
+    `  };`,
+    `});`,
     ``,
     `// ─── Depth → Granularity mapping ─────────────────────────────────────────────`,
     dtgConst,
diff --git a/sdk/src/configuration/index.ts b/sdk/src/configuration/index.ts
index ea85c95cf..8e4f9a9a2 100644
--- a/sdk/src/configuration/index.ts
+++ b/sdk/src/configuration/index.ts
@@ -41,7 +41,16 @@ export interface DynamicKeyPattern {
 }
 
 export const DYNAMIC_KEY_PATTERNS: readonly DynamicKeyPattern[] = _schemaManifest.dynamicKeyPatterns.map(
-  (p) => ({ ...p, test: (key: string) => new RegExp(p.source).test(key) }),
+  (p) => {
+    const pattern = new RegExp(p.source);
+    return {
+      ...p,
+      test: (key: string) => {
+        pattern.lastIndex = 0;
+        return pattern.test(key);
+      },
+    };
+  },
 );
 
 // ─── Types ───────────────────────────────────────────────────────────────────
@@ -305,6 +314,11 @@ export async function migrateOnDisk(cwd: string, workstream?: string): Promise<M
     }
   }
 
-  writeFileSync(configPath, JSON.stringify(result, null, 2));
+  try {
+    writeFileSync(configPath, JSON.stringify(result, null, 2));
+  } catch (err) {
+    const msg = err instanceof Error ? err.message : String(err);
+    throw new Error(`Failed to write migrated config at ${configPath}: ${msg}`);
+  }
   return { migrated: true, normalizations, wrote: configPath };
 }