diff --git a/authentik/sources/plex/api.py b/authentik/sources/plex/api.py
index 01b3c1961..a9501132c 100644
--- a/authentik/sources/plex/api.py
+++ b/authentik/sources/plex/api.py
@@ -1,9 +1,27 @@
 """Plex Source Serializer"""
-from rest_framework.viewsets import ModelViewSet
+from urllib.parse import urlencode
 
+from django.http import Http404
+from django.shortcuts import get_object_or_404
+from drf_yasg import openapi
+from drf_yasg.utils import swagger_auto_schema
+from requests import RequestException, get
+from rest_framework.decorators import action
+from rest_framework.fields import CharField
+from rest_framework.permissions import AllowAny
+from rest_framework.request import Request
+from rest_framework.response import Response
+from rest_framework.viewsets import ModelViewSet
+from structlog.stdlib import get_logger
+
+from authentik.api.decorators import permission_required
 from authentik.core.api.sources import SourceSerializer
+from authentik.core.api.utils import PassiveSerializer
+from authentik.flows.challenge import ChallengeTypes, RedirectChallenge
 from authentik.sources.plex.models import PlexSource
 
+LOGGER = get_logger()
+
 
 class PlexSourceSerializer(SourceSerializer):
     """Plex Source Serializer"""
@@ -13,9 +31,70 @@ class PlexSourceSerializer(SourceSerializer):
         fields = SourceSerializer.Meta.fields + ["client_id", "allowed_servers"]
 
 
+class PlexTokenRedeemSerializer(PassiveSerializer):
+    """Serializer to redeem a plex token"""
+
+    plex_token = CharField()
+
+
 class PlexSourceViewSet(ModelViewSet):
     """Plex source Viewset"""
 
     queryset = PlexSource.objects.all()
     serializer_class = PlexSourceSerializer
     lookup_field = "slug"
+
+    @permission_required(None)
+    @swagger_auto_schema(
+        request_body=PlexTokenRedeemSerializer(),
+        responses={200: RedirectChallenge(), 404: "Token not found"},
+        manual_parameters=[
+            openapi.Parameter(
+                name="slug",
+                in_=openapi.IN_QUERY,
+                type=openapi.TYPE_STRING,
+            )
+        ],
+    )
+    @action(
+        methods=["POST"],
+        detail=False,
+        pagination_class=None,
+        filter_backends=[],
+        permission_classes=[AllowAny],
+    )
+    def redeem_token(self, request: Request) -> Response:
+        """Redeem a plex token, check it's access to resources against what's allowed
+        for the source, and redirect to an authentication/enrollment flow."""
+        source: PlexSource = get_object_or_404(
+            PlexSource, slug=request.query_params.get("slug", "")
+        )
+        plex_token = request.data.get("plex_token", None)
+        if not plex_token:
+            raise Http404
+        qs = {"X-Plex-Token": plex_token, "X-Plex-Client-Identifier": source.client_id}
+        try:
+            response = get(
+                f"https://plex.tv/api/v2/resources?{urlencode(qs)}",
+                headers={"Accept": "application/json"},
+            )
+            response.raise_for_status()
+        except RequestException as exc:
+            LOGGER.warning("Unable to fetch user resources", exc=exc)
+            raise Http404
+        else:
+            resources: list[dict] = response.json()
+            for resource in resources:
+                if resource["provides"] != "server":
+                    continue
+                if resource["clientIdentifier"] in source.allowed_servers:
+                    LOGGER.info(
+                        "Plex allowed access from server", name=resource["name"]
+                    )
+                    request.session["foo"] = "bar"
+                    break
+            return Response(
+                RedirectChallenge(
+                    {"type": ChallengeTypes.REDIRECT.value, "to": ""}
+                ).data
+            )
diff --git a/authentik/sources/plex/models.py b/authentik/sources/plex/models.py
index 7a61c801a..da66c1902 100644
--- a/authentik/sources/plex/models.py
+++ b/authentik/sources/plex/models.py
@@ -3,10 +3,19 @@ from django.contrib.postgres.fields import ArrayField
 from django.db import models
 from django.templatetags.static import static
 from django.utils.translation import gettext_lazy as _
+from rest_framework.fields import CharField
 from rest_framework.serializers import BaseSerializer
 
 from authentik.core.models import Source
 from authentik.core.types import UILoginButton
+from authentik.flows.challenge import Challenge, ChallengeTypes
+
+
+class PlexAuthenticationChallenge(Challenge):
+    """Challenge shown to the user in identification stage"""
+
+    client_id = CharField()
+    slug = CharField()
 
 
 class PlexSource(Source):
@@ -28,12 +37,16 @@ class PlexSource(Source):
     @property
     def ui_login_button(self) -> UILoginButton:
         return UILoginButton(
-            url="",
+            challenge=PlexAuthenticationChallenge(
+                {
+                    "type": ChallengeTypes.NATIVE.value,
+                    "component": "ak-flow-sources-plex",
+                    "client_id": self.client_id,
+                    "slug": self.slug,
+                }
+            ),
             icon_url=static("authentik/sources/plex.svg"),
             name=self.name,
-            additional_data={
-                "client_id": self.client_id,
-            },
         )
 
     class Meta:
diff --git a/swagger.yaml b/swagger.yaml
index 4819cb3b3..21486dcf4 100755
--- a/swagger.yaml
+++ b/swagger.yaml
@@ -10307,6 +10307,39 @@ paths:
       tags:
         - sources
     parameters: []
+  /sources/plex/redeem_token/:
+    post:
+      operationId: sources_plex_redeem_token
+      description: |-
+        Redeem a plex token, check it's access to resources against what's allowed
+        for the source, and redirect to an authentication/enrollment flow.
+      parameters:
+        - name: data
+          in: body
+          required: true
+          schema:
+            $ref: '#/definitions/PlexTokenRedeem'
+        - name: slug
+          in: query
+          type: string
+      responses:
+        '200':
+          description: ''
+          schema:
+            $ref: '#/definitions/RedirectChallenge'
+        '404':
+          description: Token not found
+        '400':
+          description: Invalid input.
+          schema:
+            $ref: '#/definitions/ValidationError'
+        '403':
+          description: Authentication credentials were invalid, absent or insufficient.
+          schema:
+            $ref: '#/definitions/GenericError'
+      tags:
+        - sources
+    parameters: []
   /sources/plex/{slug}/:
     get:
       operationId: sources_plex_read
@@ -17655,6 +17688,51 @@ definitions:
           title: Allowed servers
           type: string
           minLength: 1
+  PlexTokenRedeem:
+    required:
+      - plex_token
+    type: object
+    properties:
+      plex_token:
+        title: Plex token
+        type: string
+        minLength: 1
+  RedirectChallenge:
+    required:
+      - type
+      - to
+    type: object
+    properties:
+      type:
+        title: Type
+        type: string
+        enum:
+          - native
+          - shell
+          - redirect
+      component:
+        title: Component
+        type: string
+        minLength: 1
+      title:
+        title: Title
+        type: string
+        minLength: 1
+      background:
+        title: Background
+        type: string
+        minLength: 1
+      response_errors:
+        title: Response errors
+        type: object
+        additionalProperties:
+          type: array
+          items:
+            $ref: '#/definitions/ErrorDetail'
+      to:
+        title: To
+        type: string
+        minLength: 1
   SAMLSource:
     required:
       - name
diff --git a/web/src/flows/FlowExecutor.ts b/web/src/flows/FlowExecutor.ts
index 2e44b01e7..6338450ba 100644
--- a/web/src/flows/FlowExecutor.ts
+++ b/web/src/flows/FlowExecutor.ts
@@ -23,6 +23,7 @@ import "./stages/email/EmailStage";
 import "./stages/identification/IdentificationStage";
 import "./stages/password/PasswordStage";
 import "./stages/prompt/PromptStage";
+import "./sources/plex/PlexLoginInit";
 import { ShellChallenge, RedirectChallenge } from "../api/Flows";
 import { IdentificationChallenge } from "./stages/identification/IdentificationStage";
 import { PasswordChallenge } from "./stages/password/PasswordStage";
@@ -44,6 +45,7 @@ import { AccessDeniedChallenge } from "./access_denied/FlowAccessDenied";
 import { PFSize } from "../elements/Spinner";
 import { TITLE_DEFAULT } from "../constants";
 import { configureSentry } from "../api/Sentry";
+import { PlexAuthenticationChallenge } from "./sources/plex/PlexLoginInit";
 
 @customElement("ak-flow-executor")
 export class FlowExecutor extends LitElement implements StageHost {
@@ -223,6 +225,8 @@ export class FlowExecutor extends LitElement implements StageHost {
                         return html`<ak-stage-authenticator-webauthn .host=${this} .challenge=${this.challenge as WebAuthnAuthenticatorRegisterChallenge}></ak-stage-authenticator-webauthn>`;
                     case "ak-stage-authenticator-validate":
                         return html`<ak-stage-authenticator-validate .host=${this} .challenge=${this.challenge as AuthenticatorValidateStageChallenge}></ak-stage-authenticator-validate>`;
+                    case "ak-flow-sources-plex":
+                        return html`<ak-flow-sources-plex .host=${this} .challenge=${this.challenge as PlexAuthenticationChallenge}></ak-flow-sources-plex>`;
                     default:
                         break;
                 }
diff --git a/web/src/flows/sources/plex/API.ts b/web/src/flows/sources/plex/API.ts
index 26e0ce362..a3dc2306f 100644
--- a/web/src/flows/sources/plex/API.ts
+++ b/web/src/flows/sources/plex/API.ts
@@ -21,6 +21,12 @@ export const DEFAULT_HEADERS = {
     "X-Plex-Device-Vendor": "BeryJu.org",
 };
 
+export function popupCenterScreen(url: string, title: string, w: number, h: number): Window | null {
+    const top = (screen.height - h) / 4, left = (screen.width - w) / 2;
+    const popup = window.open(url, title, `scrollbars=yes,width=${w},height=${h},top=${top},left=${left}`);
+    return popup;
+}
+
 export class PlexAPIClient {
 
     token: string;
@@ -44,14 +50,38 @@ export class PlexAPIClient {
         };
     }
 
-    static async pinStatus(id: number): Promise<string> {
+    static async pinStatus(clientIdentifier: string, id: number): Promise<string | undefined> {
+        const headers = { ...DEFAULT_HEADERS, ...{
+            "X-Plex-Client-Identifier": clientIdentifier
+        }};
         const pinResponse = await fetch(`https://plex.tv/api/v2/pins/${id}`, {
-            headers: DEFAULT_HEADERS
+            headers: headers
         });
         const pin: PlexPinResponse = await pinResponse.json();
         return pin.authToken || "";
     }
 
+    static async pinPoll(clientIdentifier: string, id: number): Promise<string> {
+        const executePoll = async (
+            resolve: (authToken: string) => void,
+            reject: (e: Error) => void
+        ) => {
+            try {
+                const response = await PlexAPIClient.pinStatus(clientIdentifier, id)
+
+                if (response) {
+                    resolve(response);
+                } else {
+                    setTimeout(executePoll, 500, resolve, reject);
+                }
+            } catch (e) {
+                reject(e);
+            }
+        };
+
+        return new Promise(executePoll);
+    }
+
     async getServers(): Promise<PlexResource[]> {
         const resourcesResponse = await fetch(`https://plex.tv/api/v2/resources?X-Plex-Token=${this.token}&X-Plex-Client-Identifier=authentik`, {
             headers: DEFAULT_HEADERS
diff --git a/web/src/flows/sources/plex/PlexLoginInit.ts b/web/src/flows/sources/plex/PlexLoginInit.ts
index e357b3355..5a134933a 100644
--- a/web/src/flows/sources/plex/PlexLoginInit.ts
+++ b/web/src/flows/sources/plex/PlexLoginInit.ts
@@ -1,11 +1,45 @@
-import {customElement, LitElement} from "lit-element";
+import { Challenge } from "authentik-api";
+import {customElement, property} from "lit-element";
 import {html, TemplateResult} from "lit-html";
+import { PFSize } from "../../../elements/Spinner";
+import { BaseStage } from "../../stages/base";
+import {PlexAPIClient, popupCenterScreen} from "./API";
+import {DEFAULT_CONFIG} from "../../../api/Config";
+import { SourcesApi } from "authentik-api";
+
+export interface PlexAuthenticationChallenge extends Challenge {
+
+    client_id: string;
+    slug: string;
+
+}
 
 @customElement("ak-flow-sources-plex")
-export class PlexLoginInit extends LitElement {
+export class PlexLoginInit extends BaseStage {
 
-    render(): TemplateResult {
-        return html``;
+    @property({ attribute: false })
+    challenge?: PlexAuthenticationChallenge;
+
+    async firstUpdated(): Promise<void> {
+        const authInfo = await PlexAPIClient.getPin(this.challenge?.client_id || "");
+        const authWindow = popupCenterScreen(authInfo.authUrl, "plex auth", 550, 700);
+        PlexAPIClient.pinPoll(this.challenge?.client_id || "", authInfo.pin.id).then(token => {
+            authWindow?.close();
+            new SourcesApi(DEFAULT_CONFIG).sourcesPlexRedeemToken({
+                data: {
+                    plexToken: token,
+                },
+                slug: this.challenge?.slug || "",
+            }).then(r => {
+                window.location.assign(r.to);
+            });
+        });
+    }
+
+    renderLoading(): TemplateResult {
+        return html`<div class="ak-loading">
+            <ak-spinner size=${PFSize.XLarge}></ak-spinner>
+        </div>`;
     }
 
 }
diff --git a/web/src/pages/sources/plex/PlexSourceForm.ts b/web/src/pages/sources/plex/PlexSourceForm.ts
index bc963aee5..10c7da501 100644
--- a/web/src/pages/sources/plex/PlexSourceForm.ts
+++ b/web/src/pages/sources/plex/PlexSourceForm.ts
@@ -9,15 +9,9 @@ import "../../../elements/forms/HorizontalFormElement";
 import { ifDefined } from "lit-html/directives/if-defined";
 import { until } from "lit-html/directives/until";
 import { first, randomString } from "../../../utils";
-import { PlexAPIClient, PlexResource} from "../../../flows/sources/plex/API";
+import { PlexAPIClient, PlexResource, popupCenterScreen} from "../../../flows/sources/plex/API";
 
 
-function popupCenterScreen(url: string, title: string, w: number, h: number): Window | null {
-    const top = (screen.height - h) / 4, left = (screen.width - w) / 2;
-    const popup = window.open(url, title, `scrollbars=yes,width=${w},height=${h},top=${top},left=${left}`);
-    return popup;
-}
-
 @customElement("ak-source-plex-form")
 export class PlexSourceForm extends Form<PlexSource> {
 
@@ -64,15 +58,11 @@ export class PlexSourceForm extends Form<PlexSource> {
     async doAuth(): Promise<void> {
         const authInfo = await PlexAPIClient.getPin(this.source?.clientId);
         const authWindow = popupCenterScreen(authInfo.authUrl, "plex auth", 550, 700);
-        const timer = setInterval(() => {
-            if (authWindow?.closed) {
-                clearInterval(timer);
-                PlexAPIClient.pinStatus(authInfo.pin.id).then((token: string) => {
-                    this.plexToken = token;
-                    this.loadServers();
-                });
-            }
-        }, 500);
+        PlexAPIClient.pinPoll(this.source?.clientId || "", authInfo.pin.id).then(token => {
+            authWindow?.close();
+            this.plexToken = token;
+            this.loadServers();
+        });
     }
 
     async loadServers(): Promise<void> {