diff --git a/src/logging/structured-logging.spec.ts b/src/logging/structured-logging.spec.ts
new file mode 100644
index 00000000..edbad4c7
--- /dev/null
+++ b/src/logging/structured-logging.spec.ts
@@ -0,0 +1,172 @@
+import {
+  configureSampling,
+  resetSampler,
+  getSamplerState,
+  buildLogObject,
+} from './structured-logging';
+
+// Test formatWithSampling by creating a simple wrapper that mimics the console override
+function invokeErrorSampling(args: unknown[]): string | null {
+  let output: string | null = null;
+  const originalConfig = { firstN: 3, thenEveryM: 5 };
+
+  // We'll use configureSampling + manual sampler to test the behaviour
+  configureSampling({ firstN: 3, thenEveryM: 5 });
+
+  // We can test by calling initStructuredLogging with a custom output,
+  // but instead let's directly test via console.error after init.
+
+  return output;
+}
+
+// Alternative approach: re-import after init
+import { initStructuredLogging } from './structured-logging';
+
+describe('Error sampling / rate limiting', () => {
+  let errorOutputs: string[];
+
+  beforeAll(() => {
+    // Store original console.error
+    const origError = console.error.bind(console);
+    errorOutputs = [];
+
+    // Replace console.error with a collector
+    console.error = function (...args: unknown[]) {
+      errorOutputs.push(args.map(String).join(' '));
+      origError(...args);
+    } as typeof console.error;
+
+    initStructuredLogging('test');
+  });
+
+  afterAll(() => {
+    // Don't restore — the test suite owns the override
+  });
+
+  beforeEach(() => {
+    resetSampler();
+    configureSampling({ firstN: 3, thenEveryM: 5 });
+    errorOutputs.length = 0;
+  });
+
+  function parsedCalls(): Record<string, unknown>[] {
+    return errorOutputs.map((s) => JSON.parse(s));
+  }
+
+  it('logs every error up to firstN without sampling marker', () => {
+    for (let i = 0; i < 3; i++) {
+      console.error('db connection failed', { db: 'pg' });
+    }
+
+    const outputs = parsedCalls();
+    expect(outputs).toHaveLength(3);
+    outputs.forEach((out, idx) => {
+      expect(out.message).toBe('db connection failed');
+      expect(out.occurrenceCount).toBe(idx + 1);
+      expect(out.sampled).toBeUndefined();
+    });
+  });
+
+  it('samples after firstN, logging 1-in-M with occurrenceCount', () => {
+    for (let i = 0; i < 13; i++) {
+      console.error('timeout');
+    }
+
+    const outputs = parsedCalls();
+    expect(outputs).toHaveLength(5);
+
+    expect(outputs[0].occurrenceCount).toBe(1);
+    expect(outputs[0].sampled).toBeUndefined();
+    expect(outputs[1].occurrenceCount).toBe(2);
+    expect(outputs[1].sampled).toBeUndefined();
+    expect(outputs[2].occurrenceCount).toBe(3);
+    expect(outputs[2].sampled).toBeUndefined();
+    expect(outputs[3].occurrenceCount).toBe(8);
+    expect(outputs[3].sampled).toBe(true);
+    expect(outputs[4].occurrenceCount).toBe(13);
+    expect(outputs[4].sampled).toBe(true);
+  });
+
+  it('tracks different message keys independently', () => {
+    for (let i = 0; i < 6; i++) {
+      console.error('error-a');
+      console.error('error-b');
+    }
+
+    const outputs = parsedCalls();
+    const aCalls = outputs.filter((o) => o.message === 'error-a');
+    const bCalls = outputs.filter((o) => o.message === 'error-b');
+    expect(aCalls).toHaveLength(3);
+    expect(bCalls).toHaveLength(3);
+    expect(outputs).toHaveLength(6);
+  });
+
+  it('uses Error.message as sampler key when an Error is passed', () => {
+    for (let i = 0; i < 6; i++) {
+      console.error(new Error('err occurred'));
+    }
+
+    const outputs = parsedCalls();
+    expect(outputs).toHaveLength(3);
+    outputs.forEach((o, idx) => {
+      expect(o.data).toEqual({ message: 'err occurred', stack: expect.any(String) });
+      expect(o.occurrenceCount).toBe(idx + 1);
+    });
+  });
+
+  it('does not sample non-error levels', () => {
+    for (let i = 0; i < 10; i++) {
+      console.info('info msg');
+      console.warn('warn msg');
+      console.debug('debug msg');
+    }
+
+    expect(getSamplerState().size).toBe(0);
+  });
+
+  it('configureSampling updates thresholds', () => {
+    configureSampling({ firstN: 1, thenEveryM: 2 });
+
+    for (let i = 0; i < 7; i++) {
+      console.error('err');
+    }
+
+    const outputs = parsedCalls();
+    expect(outputs).toHaveLength(4);
+    expect(outputs[0].occurrenceCount).toBe(1);
+    expect(outputs[0].sampled).toBeUndefined();
+    expect(outputs[1].occurrenceCount).toBe(3);
+    expect(outputs[1].sampled).toBe(true);
+    expect(outputs[2].occurrenceCount).toBe(5);
+    expect(outputs[2].sampled).toBe(true);
+    expect(outputs[3].occurrenceCount).toBe(7);
+    expect(outputs[3].sampled).toBe(true);
+  });
+
+  it('resetSampler clears all state', () => {
+    for (let i = 0; i < 6; i++) console.error('err');
+    expect(parsedCalls()).toHaveLength(3);
+
+    resetSampler();
+    errorOutputs.length = 0;
+
+    for (let i = 0; i < 6; i++) console.error('err');
+    expect(parsedCalls()).toHaveLength(3);
+  });
+
+  it('getSamplerState returns current counts', () => {
+    for (let i = 0; i < 10; i++) console.error('err-a');
+    for (let i = 0; i < 5; i++) console.error('err-b');
+
+    const state = getSamplerState();
+    expect(state.get('err-a')!.count).toBe(10);
+    expect(state.get('err-b')!.count).toBe(5);
+  });
+
+  it('buildLogObject is unaffected by sampling', () => {
+    const obj = buildLogObject('error', 'test message', { key: 'val' });
+    expect(obj.level).toBe('error');
+    expect(obj.message).toBe('test message');
+    expect(obj.meta).toEqual({ key: 'val' });
+  });
+});
diff --git a/src/logging/structured-logging.ts b/src/logging/structured-logging.ts
index 29147b81..7cef5073 100644
--- a/src/logging/structured-logging.ts
+++ b/src/logging/structured-logging.ts
@@ -1,5 +1,53 @@
 export type LogMeta = Record<string, unknown>;
 
+export interface SamplingConfig {
+  firstN: number;
+  thenEveryM: number;
+}
+
+interface SamplerEntry {
+  count: number;
+  logged: number;
+}
+
+const samplerMap = new Map<string, SamplerEntry>();
+const MAX_SAMPLER_ENTRIES = 1000;
+
+const DEFAULT_SAMPLING: SamplingConfig = {
+  firstN: 5,
+  thenEveryM: 10,
+};
+
+let _samplingConfig: SamplingConfig = { ...DEFAULT_SAMPLING };
+
+export function configureSampling(config: Partial<SamplingConfig>): void {
+  if (config.firstN !== undefined) _samplingConfig.firstN = config.firstN;
+  if (config.thenEveryM !== undefined) _samplingConfig.thenEveryM = config.thenEveryM;
+}
+
+export function resetSampler(): void {
+  samplerMap.clear();
+}
+
+export function getSamplerState(): ReadonlyMap<string, Readonly<SamplerEntry>> {
+  return samplerMap as ReadonlyMap<string, Readonly<SamplerEntry>>;
+}
+
+function getSamplerKey(args: unknown[]): string | null {
+  for (const arg of args) {
+    if (typeof arg === 'string') return arg;
+    if (arg instanceof Error) return arg.message;
+  }
+  return null;
+}
+
+function evictSamplerIfNeeded(): void {
+  if (samplerMap.size >= MAX_SAMPLER_ENTRIES) {
+    const keysToDelete = Array.from(samplerMap.keys()).slice(0, Math.floor(MAX_SAMPLER_ENTRIES / 2));
+    for (const key of keysToDelete) samplerMap.delete(key);
+  }
+}
+
 function timestamp(): string {
   return new Date().toISOString();
 }
@@ -45,11 +93,76 @@ function formatStructured(level: string, service: string, args: unknown[], meta:
   }
 }
 
+function formatWithSampling(
+  level: string,
+  service: string,
+  args: unknown[],
+  originalFn: (...args: unknown[]) => void,
+): void {
+  if (level !== 'error') {
+    originalFn(formatStructured(level, service, args));
+    return;
+  }
+
+  const key = getSamplerKey(args);
+  if (key === null) {
+    originalFn(formatStructured(level, service, args));
+    return;
+  }
+
+  let entry = samplerMap.get(key);
+  if (!entry) {
+    entry = { count: 0, logged: 0 };
+    samplerMap.set(key, entry);
+  }
+  entry.count++;
+
+  const { firstN, thenEveryM } = _samplingConfig;
+  const shouldLog = entry.count <= firstN || (entry.count - firstN) % thenEveryM === 0;
+
+  if (shouldLog) {
+    entry.logged++;
+    evictSamplerIfNeeded();
+    const msgParts: unknown[] = Array.prototype.slice.call(args);
+    const message = typeof msgParts[0] === 'string' ? msgParts.shift() : undefined;
+    const extra = msgParts.length === 1 ? safeSerialize(msgParts[0]) : msgParts.map(safeSerialize);
+
+    const out: Record<string, unknown> = {
+      timestamp: timestamp(),
+      level,
+      service,
+      pid: process.pid,
+      occurrenceCount: entry.count,
+    };
+
+    if (message) out.message = message;
+    if (extra !== undefined && (Array.isArray(extra) ? extra.length > 0 : Object.keys((extra as any) || {}).length > 0)) {
+      out.data = extra;
+    }
+    if (entry.count > firstN) out.sampled = true;
+
+    try {
+      originalFn(JSON.stringify(out));
+    } catch (_err) {
+      originalFn(
+        JSON.stringify({
+          timestamp: timestamp(),
+          level,
+          service,
+          pid: process.pid,
+          message: 'failed to stringify log',
+        }),
+      );
+    }
+  }
+}
+
 let _serviceName = 'teachlink-backend';
 
 /* eslint-disable no-console */
-export function initStructuredLogging(serviceName?: string): void {
+export function initStructuredLogging(serviceName?: string, samplingConfig?: Partial<SamplingConfig>): void {
   if (serviceName) _serviceName = serviceName;
+  if (samplingConfig) configureSampling(samplingConfig);
 
   const originalLog = console.log.bind(console);
   const originalInfo = console.info.bind(console);
@@ -70,7 +183,7 @@ export function initStructuredLogging(serviceName?: string): void {
   } as typeof console.warn;
 
   console.error = function error(...args: unknown[]) {
-    originalError(formatStructured('error', _serviceName, args));
+    formatWithSampling('error', _serviceName, args, originalError);
   } as typeof console.error;
 
   console.debug = function debug(...args: unknown[]) {