diff --git a/src/context/Uploader.test.ts b/src/context/Uploader.test.ts
index cf15363..c8ea165 100644
--- a/src/context/Uploader.test.ts
+++ b/src/context/Uploader.test.ts
@@ -96,6 +96,79 @@ describe('UploaderImpl', () => {
     });
   });
 
+  test('S3 PUT XML error → parses s3Code and requestId', async () => {
+    const xml =
+      '<?xml version="1.0" encoding="UTF-8"?><Error><Code>AccessDenied</Code>' +
+      '<Message>Access Denied</Message><RequestId>ABC123XYZ</RequestId>' +
+      '<HostId>hostid==</HostId></Error>';
+    const { fetch } = recordFetch([presignResponse(), new Response(xml, { status: 403 })]);
+    const result = await new UploaderImpl({ endpoint: ENDPOINT, fetch }).upload(uploadInput.build());
+
+    expect(result.isErr()).toBe(true);
+    const err = result._unsafeUnwrapErr();
+    expect(err).toMatchObject({ kind: 's3-bad-status', status: 403, s3Code: 'AccessDenied', requestId: 'ABC123XYZ' });
+  });
+
+  test('retries a transient S3 5xx, then succeeds', async () => {
+    const { fetch, calls } = recordFetch([
+      presignResponse(),
+      new Response('<Error><Code>SlowDown</Code></Error>', { status: 503 }),
+      new Response('', { status: 200 }),
+    ]);
+    const result = await new UploaderImpl({ endpoint: ENDPOINT, fetch, retryMinTimeoutMs: 0 }).upload(
+      uploadInput.build(),
+    );
+
+    expect(result.isOk()).toBe(true);
+    expect(calls.length).toBe(3); // presign + 2 PUT attempts
+  });
+
+  test('retries a network failure during PUT, then succeeds', async () => {
+    const responses = [presignResponse(), 'throw' as const, new Response('', { status: 200 })];
+    let calls = 0;
+    const fetchFn: FetchFn = () => {
+      const next = responses[calls++];
+      if (next === 'throw') return Promise.reject(new Error('econnreset'));
+      return Promise.resolve(next as Response);
+    };
+    const result = await new UploaderImpl({ endpoint: ENDPOINT, fetch: fetchFn, retryMinTimeoutMs: 0 }).upload(
+      uploadInput.build(),
+    );
+
+    expect(result.isOk()).toBe(true);
+    expect(calls).toBe(3); // presign + failed PUT + retried PUT
+  });
+
+  test('does not retry a non-transient 403 from S3', async () => {
+    const { fetch, calls } = recordFetch([presignResponse(), new Response('access denied', { status: 403 })]);
+    const result = await new UploaderImpl({ endpoint: ENDPOINT, fetch, retryMinTimeoutMs: 0 }).upload(
+      uploadInput.build(),
+    );
+
+    expect(result.isErr()).toBe(true);
+    expect(result._unsafeUnwrapErr().kind).toBe('s3-bad-status');
+    expect(calls.length).toBe(2); // presign + single PUT, no retry
+  });
+
+  test('exhausts attempts on a persistent transient failure', async () => {
+    const { fetch, calls } = recordFetch([
+      presignResponse(),
+      new Response('<Error><Code>InternalError</Code></Error>', { status: 500 }),
+      new Response('<Error><Code>InternalError</Code></Error>', { status: 500 }),
+    ]);
+    const result = await new UploaderImpl({
+      endpoint: ENDPOINT,
+      fetch,
+      maxAttempts: 2,
+      retryMinTimeoutMs: 0,
+    }).upload(uploadInput.build());
+
+    expect(result.isErr()).toBe(true);
+    const err = result._unsafeUnwrapErr();
+    expect(err).toMatchObject({ kind: 's3-bad-status', status: 500, s3Code: 'InternalError' });
+    expect(calls.length).toBe(3); // presign + 2 PUT attempts
+  });
+
   test('network failure during presign → presign-request-failed', async () => {
     const fetchFn: FetchFn = () => Promise.reject(new Error('econnreset'));
     const result = await new UploaderImpl({ endpoint: ENDPOINT, fetch: fetchFn }).upload(uploadInput.build());
diff --git a/src/context/Uploader.ts b/src/context/Uploader.ts
index f4bb486..eec2113 100644
--- a/src/context/Uploader.ts
+++ b/src/context/Uploader.ts
@@ -8,7 +8,7 @@ export type UploadError =
   | { kind: 'presign-bad-status'; status: number; body: string }
   | { kind: 'presign-bad-response'; message: string }
   | { kind: 's3-put-failed'; message: string }
-  | { kind: 's3-bad-status'; status: number; body: string };
+  | { kind: 's3-bad-status'; status: number; body: string; s3Code?: string; requestId?: string };
 
 export interface UploadInput {
   readonly bytes: Uint8Array;
@@ -31,6 +31,8 @@ export type FetchFn = (url: string, init?: RequestInit) => Promise<Response>;
 interface UploaderImplOptions {
   readonly endpoint?: string;
   readonly fetch?: FetchFn;
+  readonly maxAttempts?: number;
+  readonly retryMinTimeoutMs?: number;
 }
 
 interface PresignResponse {
@@ -42,18 +44,37 @@ interface PresignResponse {
 export class UploaderImpl implements Uploader {
   readonly #endpoint: string;
   readonly #fetch: FetchFn;
+  readonly #maxAttempts: number;
+  readonly #retryMinTimeoutMs: number;
 
   constructor(options: UploaderImplOptions = {}) {
     this.#endpoint = options.endpoint ?? DEFAULT_UPLOAD_ENDPOINT;
     this.#fetch = options.fetch ?? fetch;
+    this.#maxAttempts = options.maxAttempts ?? 4;
+    this.#retryMinTimeoutMs = options.retryMinTimeoutMs ?? 500;
   }
 
   upload(input: UploadInput): ResultAsync<UploadResult, UploadError> {
     return this.#requestPresign(input).andThen((presign) =>
-      this.#putToS3(presign.presignedUrl, input.bytes).map(() => ({ uploadId: presign.uploadId })),
+      this.#putToS3WithRetry(presign.presignedUrl, input.bytes).map(() => ({ uploadId: presign.uploadId })),
     );
   }
 
+  // The bytes are buffered in memory, so the PUT is safely replayable. Retry only
+  // the transient S3 outcomes (RequestTimeout/SlowDown/5xx, network errors) —
+  // see isRetryableUploadError; 4xx signature/permission failures fail fast.
+  // Backoff is exponential from retryMinTimeoutMs; attempts cap at maxAttempts.
+  #putToS3WithRetry(url: string, bytes: Uint8Array, attempt = 1): ResultAsync<void, UploadError> {
+    return this.#putToS3(url, bytes).orElse((err) => {
+      if (attempt >= this.#maxAttempts || !isRetryableUploadError(err)) {
+        return errAsync<void, UploadError>(err);
+      }
+      return delay(this.#retryMinTimeoutMs * 2 ** (attempt - 1)).andThen(() =>
+        this.#putToS3WithRetry(url, bytes, attempt + 1),
+      );
+    });
+  }
+
   #requestPresign(input: UploadInput): ResultAsync<PresignResponse, UploadError> {
     const body = JSON.stringify({
       owner: input.owner,
@@ -95,7 +116,7 @@ export class UploaderImpl implements Uploader {
     ).andThen((res) => {
       if (!res.ok) {
         return ResultAsync.fromSafePromise(res.text().catch(() => '')).andThen((text) =>
-          errAsync<void, UploadError>({ kind: 's3-bad-status', status: res.status, body: text }),
+          errAsync<void, UploadError>({ kind: 's3-bad-status', status: res.status, body: text, ...parseS3Error(text) }),
         );
       }
       return okAsync<void, UploadError>(undefined);
@@ -126,6 +147,48 @@ function isObject(value: unknown): value is Record<string, unknown> {
   return typeof value === 'object' && value !== null && !Array.isArray(value);
 }
 
+const delay = (ms: number): ResultAsync<void, never> =>
+  ResultAsync.fromSafePromise(new Promise<void>((resolve) => setTimeout(resolve, ms)));
+
+function isRetryableUploadError(err: UploadError): boolean {
+  switch (err.kind) {
+    case 's3-put-failed':
+      return true;
+    case 's3-bad-status':
+      return err.status === 429 || err.status >= 500 || err.s3Code === 'RequestTimeout';
+    default:
+      return false;
+  }
+}
+
+// S3 errors are XML; we pull the machine-readable <Code> and <RequestId> (cause + AWS
+// support handle) but drop the body, which echoes the owner/email object key.
+function parseS3Error(body: string): { s3Code?: string; requestId?: string } {
+  const s3Code = body.match(/<Code>([^<]+)<\/Code>/)?.[1];
+  const requestId = body.match(/<RequestId>([^<]+)<\/RequestId>/)?.[1];
+  return { ...(s3Code ? { s3Code } : {}), ...(requestId ? { requestId } : {}) };
+}
+
+// Privacy-safe telemetry: omits the raw S3 body and presigned URL (both embed the
+// owner/email object key). Network error messages are safe to include.
+export function uploadErrorTelemetry(err: UploadError): Record<string, string | number> {
+  switch (err.kind) {
+    case 'presign-request-failed':
+    case 'presign-bad-response':
+    case 's3-put-failed':
+      return { error_kind: err.kind, error_message: err.message.slice(0, 300) };
+    case 'presign-bad-status':
+      return { error_kind: err.kind, status: err.status };
+    case 's3-bad-status':
+      return {
+        error_kind: err.kind,
+        status: err.status,
+        ...(err.s3Code ? { s3_code: err.s3Code } : {}),
+        ...(err.requestId ? { request_id: err.requestId } : {}),
+      };
+  }
+}
+
 export function formatUploadError(err: UploadError): string {
   switch (err.kind) {
     case 'presign-request-failed':
@@ -137,6 +200,6 @@ export function formatUploadError(err: UploadError): string {
     case 's3-put-failed':
       return `failed to upload to S3: ${err.message}`;
     case 's3-bad-status':
-      return `S3 returned ${err.status}: ${err.body || '(empty body)'}`;
+      return `S3 returned ${err.status}${err.s3Code ? ` (${err.s3Code})` : ''}: ${err.body || '(empty body)'}`;
   }
 }
diff --git a/src/interactive/sharePrompt.ts b/src/interactive/sharePrompt.ts
index a350eef..3a522d9 100644
--- a/src/interactive/sharePrompt.ts
+++ b/src/interactive/sharePrompt.ts
@@ -1,6 +1,6 @@
 import type { Context } from '../context/index.ts';
 import { type Prompter, formatPromptError } from '../context/Prompter.ts';
-import { formatUploadError } from '../context/Uploader.ts';
+import { formatUploadError, uploadErrorTelemetry } from '../context/Uploader.ts';
 
 const SUPPORT_LINE = 'Reach us at founders@contextbridge.ai — or learn more at https://patchwave.ai';
 
@@ -41,7 +41,7 @@ export function showLocalReportReadyNotice(inputs: ReportReadyNoticeInputs): voi
 }
 
 export async function runSharePrompt(inputs: SharePromptInputs): Promise<ShareOutcome> {
-  const { prompter, analytics, uploader } = inputs.context;
+  const { prompter, analytics, uploader, logger } = inputs.context;
 
   prompter.note([`Scanned:      ${inputs.target}`, `HTML report:  ${inputs.htmlPath}`].join('\n'), 'Report ready');
 
@@ -92,7 +92,8 @@ export async function runSharePrompt(inputs: SharePromptInputs): Promise<ShareOu
   if (uploadResult.isErr()) {
     const message = formatUploadError(uploadResult.error);
     spinner.stop('Upload failed.');
-    analytics.capture('upload_failed', { error_kind: uploadResult.error.kind });
+    analytics.capture('upload_failed', uploadErrorTelemetry(uploadResult.error));
+    logger.warn({ err: uploadResult.error }, 'Analysis upload failed');
     prompter.error(message);
     prompter.note(
       [`Your local report is unchanged:`, `  ${inputs.htmlPath}`, '', SUPPORT_LINE].join('\n'),