diff --git a/config/config_DEPRECATED.ts b/config/config_DEPRECATED.ts
index 745d49ba..e05e5735 100644
--- a/config/config_DEPRECATED.ts
+++ b/config/config_DEPRECATED.ts
@@ -736,6 +736,9 @@ function getConfigVariablesFromEnv() {
     personalAccessKey: env[ENVIRONMENT_VARIABLES.HUBSPOT_PERSONAL_ACCESS_KEY],
     portalId: parseInt(env[ENVIRONMENT_VARIABLES.HUBSPOT_PORTAL_ID] || '', 10),
     refreshToken: env[ENVIRONMENT_VARIABLES.HUBSPOT_REFRESH_TOKEN],
+    httpTimeout: env[ENVIRONMENT_VARIABLES.HTTP_TIMEOUT]
+      ? parseInt(env[ENVIRONMENT_VARIABLES.HTTP_TIMEOUT] as string)
+      : undefined,
     env: getValidEnv(
       env[ENVIRONMENT_VARIABLES.HUBSPOT_ENVIRONMENT] as Environment
     ),
@@ -745,8 +748,9 @@ function getConfigVariablesFromEnv() {
 function generatePersonalAccessKeyConfig(
   portalId: number,
   personalAccessKey: string,
-  env: Environment
-): { portals: Array<CLIAccount_DEPRECATED> } {
+  env: Environment,
+  httpTimeout?: number
+): { portals: Array<CLIAccount_DEPRECATED>; httpTimeout?: number } {
   return {
     portals: [
       {
@@ -756,6 +760,7 @@ function generatePersonalAccessKeyConfig(
         env,
       },
     ],
+    httpTimeout,
   };
 }
 
@@ -765,8 +770,9 @@ function generateOauthConfig(
   clientSecret: string,
   refreshToken: string,
   scopes: Array<string>,
-  env: Environment
-): { portals: Array<OAuthAccount_DEPRECATED> } {
+  env: Environment,
+  httpTimeout?: number
+): { portals: Array<OAuthAccount_DEPRECATED>; httpTimeout?: number } {
   return {
     portals: [
       {
@@ -783,6 +789,7 @@ function generateOauthConfig(
         env,
       },
     ],
+    httpTimeout,
   };
 }
 
@@ -816,6 +823,7 @@ export function loadConfigFromEnvironment({
     portalId,
     refreshToken,
     env,
+    httpTimeout,
   } = getConfigVariablesFromEnv();
   const unableToLoadEnvConfigError =
     'Unable to load config from environment variables.';
@@ -825,8 +833,19 @@ export function loadConfigFromEnvironment({
     return;
   }
 
+  if (httpTimeout && httpTimeout < MIN_HTTP_TIMEOUT) {
+    throw new Error(
+      `The HTTP timeout value ${httpTimeout} is invalid. The value must be a number greater than ${MIN_HTTP_TIMEOUT}.`
+    );
+  }
+
   if (personalAccessKey) {
-    return generatePersonalAccessKeyConfig(portalId, personalAccessKey, env);
+    return generatePersonalAccessKeyConfig(
+      portalId,
+      personalAccessKey,
+      env,
+      httpTimeout
+    );
   } else if (clientId && clientSecret && refreshToken) {
     return generateOauthConfig(
       portalId,
@@ -834,7 +853,8 @@ export function loadConfigFromEnvironment({
       clientSecret,
       refreshToken,
       OAUTH_SCOPES.map(scope => scope.value),
-      env
+      env,
+      httpTimeout
     );
   } else if (apiKey) {
     return generateApiKeyConfig(portalId, apiKey, env);
diff --git a/constants/environments.ts b/constants/environments.ts
index d2730e92..cb704fa2 100644
--- a/constants/environments.ts
+++ b/constants/environments.ts
@@ -12,4 +12,5 @@ export const ENVIRONMENT_VARIABLES = {
   HUBSPOT_PORTAL_ID: 'HUBSPOT_PORTAL_ID',
   HUBSPOT_REFRESH_TOKEN: 'HUBSPOT_REFRESH_TOKEN',
   HUBSPOT_ENVIRONMENT: 'HUBSPOT_ENVIRONMENT',
+  HTTP_TIMEOUT: 'HTTP_TIMEOUT',
 } as const;
diff --git a/errors/apiErrors.ts b/errors/apiErrors.ts
index a6f1570a..025d3c2b 100644
--- a/errors/apiErrors.ts
+++ b/errors/apiErrors.ts
@@ -19,7 +19,13 @@ export function isSpecifiedError(
     statusCode,
     category,
     subCategory,
-  }: { statusCode?: number; category?: string; subCategory?: string }
+    code,
+  }: {
+    statusCode?: number;
+    category?: string;
+    subCategory?: string;
+    code?: string;
+  }
 ): boolean {
   // eslint-disable-next-line @typescript-eslint/no-explicit-any
   const error = (err && (err.cause as AxiosError<any>)) || err;
@@ -27,8 +33,15 @@ export function isSpecifiedError(
   const categoryErr = !category || error.response?.data?.category === category;
   const subCategoryErr =
     !subCategory || error.response?.data?.subCategory === subCategory;
+  const codeError = !code || error.code === code;
 
-  return error.isAxiosError && statusCodeErr && categoryErr && subCategoryErr;
+  return (
+    error.isAxiosError &&
+    statusCodeErr &&
+    categoryErr &&
+    subCategoryErr &&
+    codeError
+  );
 }
 
 export function isMissingScopeError(err: Error | AxiosError): boolean {
@@ -39,6 +52,10 @@ export function isGatingError(err: Error | AxiosError): boolean {
   return isSpecifiedError(err, { statusCode: 403, category: 'GATED' });
 }
 
+export function isTimeoutError(err: Error | AxiosError): boolean {
+  return isSpecifiedError(err, { code: 'ETIMEDOUT' });
+}
+
 // eslint-disable-next-line @typescript-eslint/no-explicit-any
 export function isApiUploadValidationError(err: AxiosError<any>): boolean {
   return (
diff --git a/http/__tests__/index.ts b/http/__tests__/index.ts
index 9ddef4b7..cf12d8b2 100644
--- a/http/__tests__/index.ts
+++ b/http/__tests__/index.ts
@@ -148,6 +148,9 @@ describe('http/index', () => {
         params: {
           portalId: 123,
         },
+        transitional: {
+          clarifyTimeoutError: true,
+        },
       });
     });
     it('adds authorization header when using a user token', async () => {
@@ -182,6 +185,9 @@ describe('http/index', () => {
         params: {
           portalId: 123,
         },
+        transitional: {
+          clarifyTimeoutError: true,
+        },
       });
     });
 
@@ -215,6 +221,9 @@ describe('http/index', () => {
           portalId: 123,
           hapikey: 'abc',
         },
+        transitional: {
+          clarifyTimeoutError: true,
+        },
       });
     });
   });
diff --git a/http/getAxiosConfig.ts b/http/getAxiosConfig.ts
index ada6b88b..289b264c 100644
--- a/http/getAxiosConfig.ts
+++ b/http/getAxiosConfig.ts
@@ -9,6 +9,10 @@ export const DEFAULT_USER_AGENT_HEADERS = {
   'User-Agent': `HubSpot Local Dev Lib/${version}`,
 };
 
+const DEFAULT_TRANSITIONAL = {
+  clarifyTimeoutError: true,
+};
+
 export function getAxiosConfig(
   options: AxiosConfigOptions
 ): AxiosRequestConfig {
@@ -26,6 +30,7 @@ export function getAxiosConfig(
       ...(headers || {}),
     },
     timeout: httpTimeout || 15000,
+    transitional: DEFAULT_TRANSITIONAL,
     ...rest,
   };
 }
diff --git a/lib/fileMapper.ts b/lib/fileMapper.ts
index 33c35f9b..4b026895 100644
--- a/lib/fileMapper.ts
+++ b/lib/fileMapper.ts
@@ -22,6 +22,7 @@ import {
   FileMapperInputOptions,
 } from '../types/Files';
 import { throwFileSystemError } from '../errors/fileSystemErrors';
+import { isTimeoutError } from '../errors/apiErrors';
 import { BaseError } from '../types/Error';
 import { i18n } from '../utils/lang';
 
@@ -264,10 +265,6 @@ async function writeFileMapperNode(
   return true;
 }
 
-function isTimeout(err: BaseError): boolean {
-  return !!err && (err.status === 408 || err.code === 'ESOCKETTIMEDOUT');
-}
-
 async function downloadFile(
   accountId: number,
   src: string,
@@ -308,7 +305,7 @@ async function downloadFile(
     );
   } catch (err) {
     const error = err as AxiosError;
-    if (isHubspot && isTimeout(error)) {
+    if (isHubspot && isTimeoutError(error)) {
       throwErrorWithMessage(`${i18nKey}.errors.assetTimeout`, {}, error);
     } else {
       throwErrorWithMessage(
@@ -332,22 +329,13 @@ export async function fetchFolderFromApi(
       src,
     });
   }
-  try {
-    const srcPath = isRoot ? '@root' : src;
-    const queryValues = getFileMapperQueryValues(mode, options);
-    const node = isHubspot
-      ? await downloadDefault(accountId, srcPath, queryValues)
-      : await download(accountId, srcPath, queryValues);
-    logger.log(i18n(`${i18nKey}.folderFetch`, { src, accountId }));
-    return node;
-  } catch (err) {
-    const error = err as BaseError;
-    if (isHubspot && isTimeout(error)) {
-      throwErrorWithMessage(`${i18nKey}.errors.assetTimeout`, {}, error);
-    } else {
-      throwError(error);
-    }
-  }
+  const srcPath = isRoot ? '@root' : src;
+  const queryValues = getFileMapperQueryValues(mode, options);
+  const node = isHubspot
+    ? await downloadDefault(accountId, srcPath, queryValues)
+    : await download(accountId, srcPath, queryValues);
+  logger.log(i18n(`${i18nKey}.folderFetch`, { src, accountId }));
+  return node;
 }
 
 async function downloadFolder(
@@ -401,11 +389,16 @@ async function downloadFolder(
       throwErrorWithMessage(`${i18nKey}.errors.incompleteFetch`, { src });
     }
   } catch (err) {
-    throwErrorWithMessage(
-      `${i18nKey}.errors.failedToFetchFolder`,
-      { src, dest: destPath },
-      err as AxiosError
-    );
+    const error = err as AxiosError;
+    if (isTimeoutError(error)) {
+      throwErrorWithMessage(`${i18nKey}.errors.assetTimeout`, {}, error);
+    } else {
+      throwErrorWithMessage(
+        `${i18nKey}.errors.failedToFetchFolder`,
+        { src, dest: destPath },
+        err as AxiosError
+      );
+    }
   }
 }