diff --git a/packages/arcgis-rest-auth/test/UserSession.test.ts b/packages/arcgis-rest-auth/test/UserSession.test.ts
index 96644ef068..64fa878dd3 100644
--- a/packages/arcgis-rest-auth/test/UserSession.test.ts
+++ b/packages/arcgis-rest-auth/test/UserSession.test.ts
@@ -456,14 +456,6 @@ describe("UserSession", () => {
         }
       });
 
-      fetchMock.post("https://gis.city.gov/sharing/generateToken", {
-        error: {
-          code: 400,
-          message: "Unable to generate token",
-          details: ["Unable to generate token for this server"]
-        }
-      });
-
       session
         .getToken(
           "https://gisservices.city.gov/public/rest/services/trees/FeatureServer/0/query"
@@ -491,6 +483,17 @@ describe("UserSession", () => {
         fullVersion: "10.5.1.120"
       });
 
+      fetchMock.post(
+        "https://gisservices.city.gov/public/rest/services/trees/FeatureServer/0/query",
+        {
+          error: {
+            code: 499,
+            message: "Token Required",
+            details: []
+          }
+        }
+      );
+
       request(
         "https://gisservices.city.gov/public/rest/services/trees/FeatureServer/0/query",
         {
@@ -512,37 +515,6 @@ describe("UserSession", () => {
         done();
       });
     });
-
-    it("should throw an ArcGISAuthError when no owning system is advertised", done => {
-      const session = new UserSession({
-        clientId: "id",
-        token: "token",
-        refreshToken: "refresh",
-        tokenExpires: YESTERDAY
-      });
-
-      fetchMock.post("https://gisservices.city.gov/public/rest/info", {
-        currentVersion: 10.51,
-        fullVersion: "10.5.1.120",
-        authInfo: {
-          isTokenBasedSecurity: true,
-          tokenServicesUrl: "https://gis.city.gov/sharing/generateToken"
-        }
-      });
-
-      session
-        .getToken(
-          "https://gisservices.city.gov/public/rest/services/trees/FeatureServer/0/query"
-        )
-        .catch(e => {
-          expect(e.name).toEqual(ErrorTypes.ArcGISAuthError);
-          expect(e.code).toEqual("NOT_FEDERATED");
-          expect(e.message).toEqual(
-            "NOT_FEDERATED: https://gisservices.city.gov/public/rest/services/trees/FeatureServer/0/query is not federated with any portal and is not explicitly trusted."
-          );
-          done();
-        });
-    });
   });
 
   describe(".refreshSession()", () => {
diff --git a/packages/arcgis-rest-request/src/request.ts b/packages/arcgis-rest-request/src/request.ts
index c73af84665..1b39486793 100644
--- a/packages/arcgis-rest-request/src/request.ts
+++ b/packages/arcgis-rest-request/src/request.ts
@@ -6,6 +6,7 @@ import { encodeQueryString } from "./utils/encode-query-string";
 import { requiresFormData } from "./utils/process-params";
 import { checkForErrors } from "./utils/check-for-errors";
 import { ArcGISRequestError } from "./utils/ArcGISRequestError";
+import { ArcGISAuthError } from "./utils/ArcGISAuthError";
 import { IRequestOptions } from "./utils/IRequestOptions";
 import { IParams } from "./utils/IParams";
 import { warn } from "./utils/warn";
@@ -130,6 +131,8 @@ export function request(
     ...options.params
   };
 
+  let originalAuthError: ArcGISAuthError = null;
+
   const fetchOptions: RequestInit = {
     method: httpMethod,
     /* ensures behavior mimics XMLHttpRequest.
@@ -139,11 +142,20 @@ export function request(
 
   return (authentication
     ? authentication.getToken(url, { fetch: options.fetch }).catch(err => {
-        /* if necessary, append original request url and
-         requestOptions to the error thrown by getToken() */
+        /**
+         * append original request url and requestOptions
+         * to the error thrown by getToken()
+         * to assist with retrying
+         */
         err.url = url;
         err.options = options;
-        throw err;
+        /**
+         * if an attempt is made to talk to an unfederated server
+         * first try the request anonymously. if a 'token required'
+         * error is thrown, throw the UNFEDERATED error then.
+         */
+        originalAuthError = err;
+        return Promise.resolve("");
       })
     : Promise.resolve("")
   )
@@ -230,7 +242,7 @@ export function request(
     })
     .then(data => {
       if ((params.f === "json" || params.f === "geojson") && !rawResponse) {
-        return checkForErrors(data, url, params, options);
+        return checkForErrors(data, url, params, options, originalAuthError);
       } else {
         return data;
       }
diff --git a/packages/arcgis-rest-request/src/utils/check-for-errors.ts b/packages/arcgis-rest-request/src/utils/check-for-errors.ts
index 6604ada9d8..429d2fb031 100644
--- a/packages/arcgis-rest-request/src/utils/check-for-errors.ts
+++ b/packages/arcgis-rest-request/src/utils/check-for-errors.ts
@@ -16,7 +16,8 @@ export function checkForErrors(
   response: any,
   url?: string,
   params?: IParams,
-  options?: IRequestOptions
+  options?: IRequestOptions,
+  originalAuthError?: ArcGISAuthError
 ): any {
   // this is an error message from billing.arcgis.com backend
   if (response.code >= 400) {
@@ -35,7 +36,11 @@ export function checkForErrors(
       messageCode === "GWM_0003" ||
       (code === 400 && message === "Unable to generate token.")
     ) {
-      throw new ArcGISAuthError(message, errorCode, response, url, options);
+      if (originalAuthError) {
+        throw originalAuthError;
+      } else {
+        throw new ArcGISAuthError(message, errorCode, response, url, options);
+      }
     }
 
     throw new ArcGISRequestError(message, errorCode, response, url, options);