diff --git a/packages/basic-crawler/src/internals/basic-crawler.ts b/packages/basic-crawler/src/internals/basic-crawler.ts
index de2b582b192..1d26d017499 100644
--- a/packages/basic-crawler/src/internals/basic-crawler.ts
+++ b/packages/basic-crawler/src/internals/basic-crawler.ts
@@ -39,8 +39,10 @@ import {
     purgeDefaultStorages,
     validators,
     RetryRequestError,
+    SessionError,
 } from '@crawlee/core';
 import type { Dictionary, Awaitable, BatchAddRequestsResult, SetStatusMessageOptions } from '@crawlee/types';
+import { ROTATE_PROXY_ERRORS } from '@crawlee/utils';
 import type { Method, OptionsInit } from 'got-scraping';
 import { gotScraping } from 'got-scraping';
 import ow, { ArgumentError } from 'ow';
@@ -217,6 +219,15 @@ export interface BasicCrawlerOptions<Context extends CrawlingContext = BasicCraw
      */
     maxRequestRetries?: number;
 
+    /**
+     * Maximum number of session rotations per request.
+     * The crawler will automatically rotate the session in case of a proxy error or if it gets blocked by the website.
+     *
+     * The session rotations are not counted towards the {@apilink BasicCrawlerOptions.maxRequestRetries|`maxRequestRetries`} limit.
+     * @default 10
+     */
+    maxSessionRotations?: number;
+
     /**
      * Maximum number of pages that the crawler will open. The crawl will stop when this limit is reached.
      * This value should always be set in order to prevent infinite loops in misconfigured crawlers.
@@ -423,6 +434,7 @@ export class BasicCrawler<Context extends CrawlingContext = BasicCrawlingContext
     protected requestHandlerTimeoutMillis!: number;
     protected internalTimeoutMillis: number;
     protected maxRequestRetries: number;
+    protected maxSessionRotations: number;
     protected handledRequestsCount: number;
     protected statusMessageLoggingInterval: number;
     protected statusMessageCallback?: StatusMessageCallback;
@@ -451,6 +463,7 @@ export class BasicCrawler<Context extends CrawlingContext = BasicCrawlingContext
         // TODO: remove in a future release
         handleFailedRequestFunction: ow.optional.function,
         maxRequestRetries: ow.optional.number,
+        maxSessionRotations: ow.optional.number,
         maxRequestsPerCrawl: ow.optional.number,
         autoscaledPoolOptions: ow.optional.object,
         sessionPoolOptions: ow.optional.object,
@@ -481,6 +494,7 @@ export class BasicCrawler<Context extends CrawlingContext = BasicCrawlingContext
             requestList,
             requestQueue,
             maxRequestRetries = 3,
+            maxSessionRotations = 10,
             maxRequestsPerCrawl,
             autoscaledPoolOptions = {},
             keepAlive,
@@ -575,6 +589,7 @@ export class BasicCrawler<Context extends CrawlingContext = BasicCrawlingContext
         }
 
         this.maxRequestRetries = maxRequestRetries;
+        this.maxSessionRotations = maxSessionRotations;
         this.handledRequestsCount = 0;
         this.stats = new Statistics({ logMessage: `${log.getOptions().prefix} request statistics:`, config });
         this.sessionPoolOptions = {
@@ -655,6 +670,16 @@ export class BasicCrawler<Context extends CrawlingContext = BasicCrawlingContext
         this.autoscaledPoolOptions = { ...autoscaledPoolOptions, ...basicCrawlerAutoscaledPoolConfiguration };
     }
 
+    /**
+     * Checks if the given error is a proxy error by comparing its message to a list of known proxy error messages.
+     * Used for retrying requests that failed due to proxy errors.
+     *
+     * @param error The error to check.
+     */
+    protected isProxyError(error: Error): boolean {
+        return ROTATE_PROXY_ERRORS.some((x: string) => (this._getMessageFromError(error) as any)?.includes(x));
+    }
+
     protected isRequestBlocked(_crawlingContext: Context) {
         throw new Error('the "isRequestBlocked" method is not implemented in this crawler.');
     }
@@ -1115,6 +1140,18 @@ export class BasicCrawler<Context extends CrawlingContext = BasicCrawlingContext
         return isRequestListFinished && isRequestQueueFinished;
     }
 
+    private async _rotateSession(crawlingContext: Context) {
+        const { request } = crawlingContext;
+
+        if ((request.sessionRotationCount ?? 0) >= this.maxSessionRotations) {
+            throw new Error(`Request failed because of proxy-related errors ${request.sessionRotationCount} times. `
+                + 'This might be caused by a misconfigured proxy or an invalid session pool configuration.');
+        }
+        request.sessionRotationCount ??= 0;
+        request.sessionRotationCount++;
+        crawlingContext.session?.retire();
+    }
+
     /**
      * Handles errors thrown by user provided requestHandler()
      */
@@ -1135,7 +1172,11 @@ export class BasicCrawler<Context extends CrawlingContext = BasicCrawlingContext
         if (shouldRetryRequest) {
             this.stats.errorTrackerRetry.add(error);
 
-            await this._tagUserHandlerError(() => this.errorHandler?.(this._augmentContextWithDeprecatedError(crawlingContext, error), error));
+            if (error instanceof SessionError) {
+                await this._rotateSession(crawlingContext);
+            } else {
+                await this._tagUserHandlerError(() => this.errorHandler?.(this._augmentContextWithDeprecatedError(crawlingContext, error), error));
+            }
 
             if (!request.noRetry) {
                 request.retryCount++;
diff --git a/packages/browser-crawler/src/internals/browser-crawler.ts b/packages/browser-crawler/src/internals/browser-crawler.ts
index 07603e07e22..c0d5be868aa 100644
--- a/packages/browser-crawler/src/internals/browser-crawler.ts
+++ b/packages/browser-crawler/src/internals/browser-crawler.ts
@@ -24,6 +24,7 @@ import {
     RequestState,
     resolveBaseUrlForEnqueueLinksFiltering,
     validators,
+    SessionError,
 } from '@crawlee/basic';
 import type {
     BrowserController,
@@ -510,8 +511,7 @@ export abstract class BrowserCrawler<
 
         if (this.retryOnBlocked) {
             if (await this.isRequestBlocked(crawlingContext)) {
-                session?.retire();
-                throw new Error('Antibot protection detected, the session has been retired.');
+                throw new SessionError();
             }
         }
 
@@ -581,6 +581,8 @@ export abstract class BrowserCrawler<
             await this._handleNavigationTimeout(crawlingContext, error as Error);
 
             crawlingContext.request.state = RequestState.ERROR;
+
+            this._throwIfProxyError(error as Error);
             throw error;
         }
         tryCancel();
@@ -619,6 +621,15 @@ export abstract class BrowserCrawler<
         await crawlingContext.page.close();
     }
 
+    /**
+     * Transforms proxy-related errors to `SessionError`.
+     */
+    protected _throwIfProxyError(error: Error) {
+        if (this.isProxyError(error)) {
+            throw new SessionError(error.message);
+        }
+    }
+
     protected abstract _navigationHandler(crawlingContext: Context, gotoOptions: GoToOptions): Promise<Context['response'] | null | undefined>;
 
     /**
diff --git a/packages/core/src/errors.ts b/packages/core/src/errors.ts
index b4312f187e6..26631745e8e 100644
--- a/packages/core/src/errors.ts
+++ b/packages/core/src/errors.ts
@@ -23,3 +23,14 @@ export class RetryRequestError extends Error {
         super(message ?? "Request is being retried at the user's request");
     }
 }
+
+/**
+ * Errors of `SessionError` type will trigger a session rotation.
+ *
+ * This error doesn't respect the `maxRequestRetries` option and has a separate limit of `maxSessionRotations`.
+ */
+export class SessionError extends RetryRequestError {
+    constructor(message?: string) {
+        super(message ?? 'Detected a session error, rotating session...');
+    }
+}
diff --git a/packages/core/src/request.ts b/packages/core/src/request.ts
index 3e2a4f9d4e3..164729ae80d 100644
--- a/packages/core/src/request.ts
+++ b/packages/core/src/request.ts
@@ -22,6 +22,7 @@ const requestOptionalPredicates = {
     payload: ow.optional.any(ow.string, ow.buffer),
     noRetry: ow.optional.boolean,
     retryCount: ow.optional.number,
+    sessionRotationCount: ow.optional.number,
     maxRetries: ow.optional.number,
     errorMessages: ow.optional.array.ofType(ow.string),
     headers: ow.optional.object,
@@ -107,6 +108,9 @@ export class Request<UserData extends Dictionary = Dictionary> {
     /** The `true` value indicates that the request will not be automatically retried on error. */
     noRetry: boolean;
 
+    /** Indicates the number of times the crawling of the request has rotated the session due to a session or a proxy error. */
+    sessionRotationCount?: number;
+
     /** Indicates the number of times the crawling of the request has been retried on error. */
     retryCount: number;
 
@@ -159,6 +163,7 @@ export class Request<UserData extends Dictionary = Dictionary> {
             payload,
             noRetry = false,
             retryCount = 0,
+            sessionRotationCount = 0,
             maxRetries,
             errorMessages = [],
             headers = {},
@@ -168,7 +173,14 @@ export class Request<UserData extends Dictionary = Dictionary> {
             keepUrlFragment = false,
             useExtendedUniqueKey = false,
             skipNavigation,
-        } = options as RequestOptions & { loadedUrl?: string; retryCount?: number; maxRetries?: number; errorMessages?: string[]; handledAt?: string | Date };
+        } = options as RequestOptions & {
+            loadedUrl?: string;
+            retryCount?: number;
+            sessionRotationCount?: number;
+            maxRetries?: number;
+            errorMessages?: string[];
+            handledAt?: string | Date;
+        };
 
         let {
             method = 'GET',
@@ -186,6 +198,7 @@ export class Request<UserData extends Dictionary = Dictionary> {
         this.payload = payload;
         this.noRetry = noRetry;
         this.retryCount = retryCount;
+        this.sessionRotationCount = sessionRotationCount;
         this.errorMessages = [...errorMessages];
         this.headers = { ...headers };
         this.handledAt = handledAt as unknown instanceof Date ? (handledAt as Date).toISOString() : handledAt!;
diff --git a/packages/http-crawler/src/internals/http-crawler.ts b/packages/http-crawler/src/internals/http-crawler.ts
index ab36f4e6943..64c74c4075b 100644
--- a/packages/http-crawler/src/internals/http-crawler.ts
+++ b/packages/http-crawler/src/internals/http-crawler.ts
@@ -25,6 +25,7 @@ import {
     validators,
     Configuration,
     RequestState,
+    SessionError,
 } from '@crawlee/basic';
 import type { Awaitable, Dictionary } from '@crawlee/types';
 import { RETRY_CSS_SELECTORS } from '@crawlee/utils';
@@ -446,11 +447,11 @@ export class HttpCrawler<Context extends InternalHttpCrawlingContext<any, any, H
             crawlingContext.parseWithCheerio ??= async () => cheerio.load(parsed.body!.toString());
 
             if (this.useSessionPool) {
-                this._throwOnBlockedRequest(session!, response.statusCode!);
+                this._throwOnBlockedRequest(crawlingContext.session!, response.statusCode!);
             }
 
             if (this.persistCookiesPerSession) {
-                session!.setCookiesFromResponse(response);
+                crawlingContext.session!.setCookiesFromResponse(response);
             }
 
             request.loadedUrl = response.url;
@@ -467,8 +468,7 @@ export class HttpCrawler<Context extends InternalHttpCrawlingContext<any, any, H
         }
 
         if (this.retryOnBlocked && await this.isRequestBlocked(crawlingContext)) {
-            crawlingContext.session?.retire();
-            throw new Error('Antibot protection detected, the session has been retired.');
+            throw new SessionError();
         }
 
         request.state = RequestState.REQUEST_HANDLER;
@@ -596,7 +596,11 @@ export class HttpCrawler<Context extends InternalHttpCrawlingContext<any, any, H
                 return undefined as unknown as PlainResponse;
             }
 
-            throw e;
+            if (this.isProxyError(e as Error)) {
+                throw new SessionError();
+            } else {
+                throw e;
+            }
         }
     }
 
diff --git a/packages/utils/src/internals/blocked.ts b/packages/utils/src/internals/blocked.ts
index d94e9d980fc..fb7b58a84f3 100644
--- a/packages/utils/src/internals/blocked.ts
+++ b/packages/utils/src/internals/blocked.ts
@@ -5,3 +5,14 @@ export const RETRY_CSS_SELECTORS = [
     'iframe[src^="https://challenges.cloudflare.com"]',
     'div#infoDiv0 a[href*="//www.google.com/policies/terms/"]',
 ];
+
+/**
+ * Content of proxy errors that should trigger a retry, as the proxy is likely getting blocked / is malfunctioning.
+ */
+export const ROTATE_PROXY_ERRORS = [
+    'ECONNRESET',
+    'ECONNREFUSED',
+    'ERR_PROXY_CONNECTION_FAILED',
+    'ERR_TUNNEL_CONNECTION_FAILED',
+    'Proxy responded with',
+];
diff --git a/test/core/crawlers/browser_crawler.test.ts b/test/core/crawlers/browser_crawler.test.ts
index 68e0cc87a97..a26457eae20 100644
--- a/test/core/crawlers/browser_crawler.test.ts
+++ b/test/core/crawlers/browser_crawler.test.ts
@@ -786,7 +786,73 @@ describe('BrowserCrawler', () => {
 
             delete process.env[ENV_VARS.PROXY_PASSWORD];
         });
+
+        test('proxy rotation on error works as expected', async () => {
+            const goodProxyUrl = 'http://good.proxy';
+            const proxyConfiguration = new ProxyConfiguration({ proxyUrls: ['http://localhost', 'http://localhost:1234', goodProxyUrl] });
+
+            const browserCrawler = new class extends BrowserCrawlerTest {
+                protected override async _navigationHandler(ctx: PuppeteerCrawlingContext): Promise<HTTPResponse | null | undefined> {
+                    const { session } = ctx;
+                    const proxyInfo = await this.proxyConfiguration.newProxyInfo(session?.id);
+
+                    if (proxyInfo.url !== goodProxyUrl) {
+                        throw new Error('ERR_PROXY_CONNECTION_FAILED');
+                    }
+
+                    return null;
+                }
+            }({
+                browserPoolOptions: {
+                    browserPlugins: [puppeteerPlugin],
+                },
+                requestList,
+                maxRequestRetries: 0,
+                maxConcurrency: 1,
+                useSessionPool: true,
+                proxyConfiguration,
+                requestHandler: async () => {},
+            });
+
+            await expect(browserCrawler.run()).resolves.not.toThrow();
+        });
+
+        test('proxy rotation on error stops after maxSessionRotations limit', async () => {
+            const proxyConfiguration = new ProxyConfiguration({ proxyUrls: ['http://localhost', 'http://localhost:1234'] });
+
+            /**
+             * The first increment is the base case when the proxy is retrieved for the first time.
+             */
+            let numberOfRotations = -1;
+            const browserCrawler = new class extends BrowserCrawlerTest {
+                protected override async _navigationHandler(ctx: PuppeteerCrawlingContext): Promise<HTTPResponse | null | undefined> {
+                    const { session } = ctx;
+                    const proxyInfo = await this.proxyConfiguration.newProxyInfo(session?.id);
+
+                    numberOfRotations++;
+
+                    if (proxyInfo.url.includes('localhost')) {
+                        throw new Error('ERR_PROXY_CONNECTION_FAILED');
+                    }
+
+                    return null;
+                }
+            }({
+                browserPoolOptions: {
+                    browserPlugins: [puppeteerPlugin],
+                },
+                requestList,
+                maxSessionRotations: 5,
+                maxConcurrency: 1,
+                proxyConfiguration,
+                requestHandler: async () => {},
+            });
+
+            await expect(browserCrawler.run()).rejects.toThrow();
+            expect(numberOfRotations).toBe(5);
+        });
     });
+
     describe('Crawling context', () => {
         const sources = ['http://example.com/'];
         let requestList: RequestList;
@@ -855,29 +921,5 @@ describe('BrowserCrawler', () => {
 
             await browserCrawler.run();
         });
-
-        test('failedRequestHandler contains proxyInfo', async () => {
-            const proxyConfiguration = new ProxyConfiguration({ proxyUrls: ['http://localhost'] });
-
-            const browserCrawler = new BrowserCrawlerTest({
-                browserPoolOptions: {
-                    browserPlugins: [puppeteerPlugin],
-                },
-                requestList,
-                maxRequestRetries: 0,
-                maxConcurrency: 1,
-                useSessionPool: true,
-                proxyConfiguration,
-                requestHandler: async () => {
-                    throw new Error('some error');
-                },
-                failedRequestHandler: async (crawlingContext) => {
-                    expect(typeof crawlingContext.proxyInfo).toEqual('object');
-                    expect(crawlingContext.proxyInfo.hasOwnProperty('url')).toEqual(true);
-                },
-            });
-
-            await browserCrawler.run();
-        });
     });
 });
diff --git a/test/core/crawlers/cheerio_crawler.test.ts b/test/core/crawlers/cheerio_crawler.test.ts
index 28bdd06e2e1..93e52365fbf 100644
--- a/test/core/crawlers/cheerio_crawler.test.ts
+++ b/test/core/crawlers/cheerio_crawler.test.ts
@@ -694,6 +694,55 @@ describe('CheerioCrawler', () => {
                 expect(proxyInfo).toEqual(await proxyConfiguration.newProxyInfo(session.id));
             }
         });
+
+        test('proxy rotation on error works as expected', async () => {
+            const goodProxyUrl = 'http://good.proxy';
+            const proxyConfiguration = new ProxyConfiguration({ proxyUrls: ['http://localhost', 'http://localhost:1234', goodProxyUrl] });
+
+            const crawler = new class extends CheerioCrawler {
+                protected override async _requestFunction({ proxyUrl }: any): Promise<any> {
+                    if (proxyUrl !== goodProxyUrl) {
+                        throw new Error('Proxy responded with 400 - Bad request');
+                    }
+
+                    return null;
+                }
+            }({
+                maxRequestRetries: 0,
+                maxConcurrency: 1,
+                useSessionPool: true,
+                proxyConfiguration,
+                requestHandler: async () => {},
+            });
+
+            await expect(crawler.run([serverAddress])).resolves.not.toThrow();
+        });
+
+        test('proxy rotation on error stops after maxSessionRotations limit', async () => {
+            const proxyConfiguration = new ProxyConfiguration({ proxyUrls: ['http://localhost', 'http://localhost:1234'] });
+
+            /**
+             * The first increment is the base case when the proxy is retrieved for the first time.
+             */
+            let numberOfRotations = -1;
+            const crawler = new CheerioCrawler({
+                proxyConfiguration,
+                maxSessionRotations: 5,
+                requestHandler: async () => {},
+            });
+
+            jest.spyOn(crawler, '_requestAsBrowser' as any).mockImplementation(async ({ proxyUrl }: any) => {
+                if (proxyUrl.includes('localhost')) {
+                    numberOfRotations++;
+                    throw new Error('Proxy responded with 400 - Bad request');
+                }
+
+                return null;
+            });
+
+            await expect(crawler.run([serverAddress])).rejects.toThrow();
+            expect(numberOfRotations).toBe(5);
+        });
     });
 
     describe('SessionPool', () => {
@@ -998,6 +1047,7 @@ describe('CheerioCrawler', () => {
             const cheerioCrawler = new CheerioCrawler({
                 requestList: requestListNew,
                 maxRequestRetries: 0,
+                maxSessionRotations: 0,
                 requestHandler: () => {},
                 failedRequestHandler: () => {},
                 useSessionPool: true,
@@ -1012,7 +1062,11 @@ describe('CheerioCrawler', () => {
                 return oldHandleRequestF.call(cheerioCrawler, opts);
             };
 
-            await cheerioCrawler.run();
+            try {
+                await cheerioCrawler.run();
+            } catch (e) {
+                // localhost proxy causes proxy errors, session rotations and finally throws, but we don't care
+            }
 
             expect(newUrlSpy).toBeCalledWith(usedSession.id);
         });
@@ -1078,26 +1132,6 @@ describe('CheerioCrawler', () => {
             });
             await cheerioCrawler.run();
         });
-
-        test('failedRequestHandler contains proxyInfo', async () => {
-            const proxyConfiguration = new ProxyConfiguration({ proxyUrls: ['http://localhost:8080'] });
-
-            const cheerioCrawler = new CheerioCrawler({
-                requestList,
-                maxRequestRetries: 0,
-                maxConcurrency: 1,
-                proxyConfiguration,
-                requestHandler: () => {
-                    throw new Error('some error');
-                },
-                failedRequestHandler: (crawlingContext) => {
-                    expect(typeof crawlingContext.proxyInfo).toEqual('object');
-                    expect(crawlingContext.proxyInfo.hasOwnProperty('url')).toEqual(true);
-                },
-                useSessionPool: true,
-            });
-            await cheerioCrawler.run();
-        });
     });
 
     describe('use', () => {