diff --git a/job_applier.mjs b/job_applier.mjs
index 53000e1..abefc2f 100644
--- a/job_applier.mjs
+++ b/job_applier.mjs
@@ -4,14 +4,13 @@
  * Reads jobs queue and applies to each new/needs_answer job
  * Run via cron or manually: node job_applier.mjs [--preview]
  */
-import { readFileSync, writeFileSync, existsSync } from 'fs';
+import { readFileSync, existsSync } from 'fs';
 import { dirname, resolve } from 'path';
 import { fileURLToPath } from 'url';
 
 const __dir = dirname(fileURLToPath(import.meta.url));
-const cfg = p => JSON.parse(readFileSync(resolve(__dir, p), 'utf8'));
 
-import { getJobsByStatus, updateJobStatus, appendLog } from './lib/queue.mjs';
+import { getJobsByStatus, updateJobStatus, appendLog, loadConfig } from './lib/queue.mjs';
 import { createBrowser } from './lib/browser.mjs';
 import { FormFiller } from './lib/form_filler.mjs';
 import { verifyLogin as liLogin, applyLinkedIn } from './lib/linkedin.mjs';
@@ -20,7 +19,7 @@ import { sendTelegram, formatApplySummary, formatUnknownQuestion } from './lib/n
 import {
   DEFAULT_REVIEW_WINDOW_MINUTES,
   APPLY_BETWEEN_DELAY_BASE, APPLY_BETWEEN_DELAY_WF_BASE,
-  APPLY_BETWEEN_DELAY_JITTER
+  APPLY_BETWEEN_DELAY_JITTER, DEFAULT_MAX_RETRIES
 } from './lib/constants.mjs';
 
 const isPreview = process.argv.includes('--preview');
@@ -28,14 +27,14 @@ const isPreview = process.argv.includes('--preview');
 async function main() {
   console.log('🚀 claw-apply: Job Applier starting\n');
 
-  const settings = cfg('config/settings.json');
-  const profile = cfg('config/profile.json');
-  const answers = existsSync(resolve(__dir, 'config/answers.json'))
-    ? JSON.parse(readFileSync(resolve(__dir, 'config/answers.json'), 'utf8'))
-    : [];
+  const settings = loadConfig(resolve(__dir, 'config/settings.json'));
+  const profile = loadConfig(resolve(__dir, 'config/profile.json'));
+  const answersPath = resolve(__dir, 'config/answers.json');
+  const answers = existsSync(answersPath) ? loadConfig(answersPath) : [];
 
   const formFiller = new FormFiller(profile, answers);
   const maxApps = settings.max_applications_per_run || Infinity;
+  const maxRetries = settings.max_retries ?? DEFAULT_MAX_RETRIES;
 
   // Preview mode: show queue and exit
   if (isPreview) {
@@ -87,10 +86,7 @@ async function main() {
           const result = await applyLinkedIn(liBrowser.page, job, formFiller);
           await handleResult(job, result, results, settings);
         } catch (e) {
-          console.log(`    ❌ Error: ${e.message?.substring(0, 80)}`);
-          updateJobStatus(job.id, 'failed', { notes: e.message?.substring(0, 80) });
-          appendLog({ ...job, status: 'failed', error: e.message?.substring(0, 80) });
-          results.failed++;
+          handleError(job, e, results, maxRetries);
         }
         await liBrowser.page.waitForTimeout(APPLY_BETWEEN_DELAY_BASE + Math.random() * APPLY_BETWEEN_DELAY_JITTER);
       }
@@ -117,10 +113,7 @@ async function main() {
           const result = await applyWellfound(wfBrowser.page, job, formFiller);
           await handleResult(job, result, results, settings);
         } catch (e) {
-          console.log(`    ❌ Error: ${e.message?.substring(0, 80)}`);
-          updateJobStatus(job.id, 'failed', { notes: e.message?.substring(0, 80) });
-          appendLog({ ...job, status: 'failed', error: e.message?.substring(0, 80) });
-          results.failed++;
+          handleError(job, e, results, maxRetries);
         }
         await wfBrowser.page.waitForTimeout(APPLY_BETWEEN_DELAY_WF_BASE + Math.random() * APPLY_BETWEEN_DELAY_JITTER);
       }
@@ -199,6 +192,20 @@ async function handleResult(job, result, results, settings) {
   }
 }
 
+function handleError(job, e, results, maxRetries) {
+  const msg = e.message?.substring(0, 80);
+  const retries = (job.retry_count || 0) + 1;
+  if (retries <= maxRetries) {
+    console.log(`    ⚠️  Error (retry ${retries}/${maxRetries}): ${msg}`);
+    updateJobStatus(job.id, 'new', { retry_count: retries, last_error: msg });
+  } else {
+    console.log(`    ❌ Error (max retries reached): ${msg}`);
+    updateJobStatus(job.id, 'failed', { retry_count: retries, notes: msg });
+    appendLog({ ...job, status: 'failed', error: msg });
+    results.failed++;
+  }
+}
+
 main().catch(e => {
   console.error('Fatal:', e.message);
   process.exit(1);
diff --git a/job_searcher.mjs b/job_searcher.mjs
index 7352c43..ead6d2c 100644
--- a/job_searcher.mjs
+++ b/job_searcher.mjs
@@ -4,14 +4,12 @@
  * Searches LinkedIn + Wellfound and populates the jobs queue
  * Run via cron or manually: node job_searcher.mjs
  */
-import { readFileSync, existsSync } from 'fs';
 import { dirname, resolve } from 'path';
 import { fileURLToPath } from 'url';
 
 const __dir = dirname(fileURLToPath(import.meta.url));
-const cfg = p => JSON.parse(readFileSync(resolve(__dir, p), 'utf8'));
 
-import { addJobs, loadQueue } from './lib/queue.mjs';
+import { addJobs, loadQueue, loadConfig } from './lib/queue.mjs';
 import { createBrowser } from './lib/browser.mjs';
 import { verifyLogin as liLogin, searchLinkedIn } from './lib/linkedin.mjs';
 import { verifyLogin as wfLogin, searchWellfound } from './lib/wellfound.mjs';
@@ -22,8 +20,8 @@ async function main() {
   console.log('🔍 claw-apply: Job Searcher starting\n');
 
   // Load config
-  const settings = cfg('config/settings.json');
-  const searchConfig = cfg('config/search_config.json');
+  const settings = loadConfig(resolve(__dir, 'config/settings.json'));
+  const searchConfig = loadConfig(resolve(__dir, 'config/search_config.json'));
 
   // First run detection: if queue is empty, use first_run_days lookback
   const isFirstRun = loadQueue().length === 0;
diff --git a/lib/constants.mjs b/lib/constants.mjs
index 4ae7295..302d09d 100644
--- a/lib/constants.mjs
+++ b/lib/constants.mjs
@@ -53,3 +53,4 @@ export const NOTIFY_RATE_LIMIT_MS = 1500;
 
 // --- Queue ---
 export const DEFAULT_REVIEW_WINDOW_MINUTES = 30;
+export const DEFAULT_MAX_RETRIES = 2;
diff --git a/lib/queue.mjs b/lib/queue.mjs
index eb401e4..b0b845a 100644
--- a/lib/queue.mjs
+++ b/lib/queue.mjs
@@ -3,13 +3,34 @@
  * Handles jobs_queue.json read/write/update
  */
 import { readFileSync, writeFileSync, existsSync, mkdirSync } from 'fs';
-import { dirname } from 'path';
+import { dirname, resolve } from 'path';
 import { fileURLToPath } from 'url';
 
 const __dir = dirname(fileURLToPath(import.meta.url));
 const QUEUE_PATH = `${__dir}/../data/jobs_queue.json`;
 const LOG_PATH = `${__dir}/../data/applications_log.json`;
 
+/**
+ * Load and validate a JSON config file. Throws with a clear message on failure.
+ */
+export function loadConfig(filePath) {
+  const resolved = resolve(filePath);
+  if (!existsSync(resolved)) {
+    throw new Error(`Config file not found: ${resolved}\nCopy the matching .example.json and fill in your values.`);
+  }
+  let raw;
+  try {
+    raw = readFileSync(resolved, 'utf8');
+  } catch (e) {
+    throw new Error(`Cannot read config file ${resolved}: ${e.message}`);
+  }
+  try {
+    return JSON.parse(raw);
+  } catch (e) {
+    throw new Error(`Invalid JSON in ${resolved}: ${e.message}`);
+  }
+}
+
 function ensureDir(path) {
   const dir = dirname(path);
   if (!existsSync(dir)) mkdirSync(dir, { recursive: true });