diff --git a/apps/webapp/app/presenters/v3/NewAlertChannelPresenter.server.ts b/apps/webapp/app/presenters/v3/NewAlertChannelPresenter.server.ts
index 5bf83bf493..b7f665ff10 100644
--- a/apps/webapp/app/presenters/v3/NewAlertChannelPresenter.server.ts
+++ b/apps/webapp/app/presenters/v3/NewAlertChannelPresenter.server.ts
@@ -1,10 +1,11 @@
 import {
-  AuthenticatableIntegration,
+  type AuthenticatableIntegration,
   OrgIntegrationRepository,
 } from "~/models/orgIntegration.server";
-import { logger } from "~/services/logger.server";
 import { BasePresenter } from "./basePresenter.server";
-import { WebClient } from "@slack/web-api";
+import { type WebClient } from "@slack/web-api";
+import { tryCatch } from "@trigger.dev/core";
+import { logger } from "~/services/logger.server";
 
 export class NewAlertChannelPresenter extends BasePresenter {
   public async call(projectId: string) {
@@ -30,42 +31,66 @@ export class NewAlertChannelPresenter extends BasePresenter {
 
     // If there is a slack integration, then we need to get a list of Slack Channels
     if (slackIntegration) {
-      const channels = await getSlackChannelsForToken(slackIntegration);
+      const [error, channels] = await tryCatch(getSlackChannelsForToken(slackIntegration));
+
+      if (error) {
+        if (isSlackError(error) && error.data.error === "token_revoked") {
+          return {
+            slack: {
+              status: "TOKEN_REVOKED" as const,
+            },
+          };
+        }
+
+        if (isSlackError(error) && error.data.error === "token_expired") {
+          return {
+            slack: {
+              status: "TOKEN_EXPIRED" as const,
+            },
+          };
+        }
+
+        logger.error("Failed fetching Slack channels for creating alerts", {
+          error,
+          slackIntegrationId: slackIntegration.id,
+        });
+
+        return {
+          slack: {
+            status: "FAILED_FETCHING_CHANNELS" as const,
+          },
+        };
+      }
 
       return {
         slack: {
           status: "READY" as const,
-          channels,
+          channels: channels ?? [],
           integrationId: slackIntegration.id,
         },
       };
-    } else {
-      if (OrgIntegrationRepository.isSlackSupported) {
-        return {
-          slack: {
-            status: "NOT_CONFIGURED" as const,
-          },
-        };
-      } else {
-        return {
-          slack: {
-            status: "NOT_AVAILABLE" as const,
-          },
-        };
-      }
     }
+
+    if (OrgIntegrationRepository.isSlackSupported) {
+      return {
+        slack: {
+          status: "NOT_CONFIGURED" as const,
+        },
+      };
+    }
+
+    return {
+      slack: {
+        status: "NOT_AVAILABLE" as const,
+      },
+    };
   }
 }
 
 async function getSlackChannelsForToken(integration: AuthenticatableIntegration) {
   const client = await OrgIntegrationRepository.getAuthenticatedClientForIntegration(integration);
-
   const channels = await getAllSlackConversations(client);
 
-  logger.debug("Received a list of slack conversations", {
-    channels,
-  });
-
   return (channels ?? [])
     .filter((channel) => !channel.is_archived)
     .filter((channel) => channel.is_channel)
@@ -100,3 +125,15 @@ async function getAllSlackConversations(client: WebClient) {
 
   return channels;
 }
+
+function isSlackError(obj: unknown): obj is { data: { error: string } } {
+  return Boolean(
+    typeof obj === "object" &&
+      obj !== null &&
+      "data" in obj &&
+      typeof obj.data === "object" &&
+      obj.data !== null &&
+      "error" in obj.data &&
+      typeof obj.data.error === "string"
+  );
+}
diff --git a/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.alerts.new.connect-to-slack.ts b/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.alerts.new.connect-to-slack.ts
index 99dc07f12a..6800ab2ed8 100644
--- a/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.alerts.new.connect-to-slack.ts
+++ b/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.alerts.new.connect-to-slack.ts
@@ -1,13 +1,11 @@
 import { type LoaderFunctionArgs } from "@remix-run/server-runtime";
 import { prisma } from "~/db.server";
-import { env } from "~/env.server";
 import { redirectWithSuccessMessage } from "~/models/message.server";
 import { OrgIntegrationRepository } from "~/models/orgIntegration.server";
 import { findProjectBySlug } from "~/models/project.server";
 import { requireUserId } from "~/services/session.server";
 import {
   EnvironmentParamSchema,
-  ProjectParamSchema,
   v3NewProjectAlertPath,
   v3NewProjectAlertPathConnectToSlackPath,
 } from "~/utils/pathBuilder";
@@ -16,6 +14,9 @@ export async function loader({ request, params }: LoaderFunctionArgs) {
   const userId = await requireUserId(request);
   const { organizationSlug, projectParam, envParam } = EnvironmentParamSchema.parse(params);
 
+  const url = new URL(request.url);
+  const shouldReinstall = url.searchParams.get("reinstall") === "true";
+
   const project = await findProjectBySlug(organizationSlug, projectParam, userId);
 
   if (!project) {
@@ -30,7 +31,8 @@ export async function loader({ request, params }: LoaderFunctionArgs) {
     },
   });
 
-  if (integration) {
+  // If integration exists and we're not reinstalling, redirect back to alerts
+  if (integration && !shouldReinstall) {
     return redirectWithSuccessMessage(
       `${v3NewProjectAlertPath({ slug: organizationSlug }, project, {
         slug: envParam,
@@ -38,15 +40,15 @@ export async function loader({ request, params }: LoaderFunctionArgs) {
       request,
       "Successfully connected your Slack workspace"
     );
-  } else {
-    // Redirect to Slack
-    return await OrgIntegrationRepository.redirectToAuthService(
-      "SLACK",
-      project.organizationId,
-      request,
-      v3NewProjectAlertPathConnectToSlackPath({ slug: organizationSlug }, project, {
-        slug: envParam,
-      })
-    );
   }
+
+  // Redirect to Slack for new installation or reinstallation
+  return await OrgIntegrationRepository.redirectToAuthService(
+    "SLACK",
+    project.organizationId,
+    request,
+    v3NewProjectAlertPathConnectToSlackPath({ slug: organizationSlug }, project, {
+      slug: envParam,
+    })
+  );
 }
diff --git a/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.alerts.new/route.tsx b/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.alerts.new/route.tsx
index 526798cd78..18ef2e522e 100644
--- a/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.alerts.new/route.tsx
+++ b/apps/webapp/app/routes/_app.orgs.$organizationSlug.projects.$projectParam.env.$envParam.alerts.new/route.tsx
@@ -356,6 +356,31 @@ export default function Page() {
                       <SlackIcon className="size-5" /> Connect to Slack
                     </span>
                   </LinkButton>
+                ) : slack.status === "TOKEN_REVOKED" || slack.status === "TOKEN_EXPIRED" ? (
+                  <div className="flex flex-col gap-4">
+                    <Callout variant="info">
+                      The Slack integration in your workspace has been revoked or has expired.
+                      Please re-connect your Slack workspace.
+                    </Callout>
+                    <LinkButton
+                      variant="tertiary/large"
+                      to={{
+                        pathname: "connect-to-slack",
+                        search: "?reinstall=true",
+                      }}
+                      fullWidth
+                    >
+                      <span className="flex items-center gap-2 text-text-bright">
+                        <SlackIcon className="size-5" /> Connect to Slack
+                      </span>
+                    </LinkButton>
+                  </div>
+                ) : slack.status === "FAILED_FETCHING_CHANNELS" ? (
+                  <div className="flex flex-col gap-4">
+                    <Callout variant="warning">
+                      Failed loading channels from Slack. Please try again later.
+                    </Callout>
+                  </div>
                 ) : (
                   <Callout variant="warning">
                     Slack integration is not available. Please contact your organization
diff --git a/apps/webapp/app/v3/services/createOrgIntegration.server.ts b/apps/webapp/app/v3/services/createOrgIntegration.server.ts
index 4db6581c9a..4f33a58fe8 100644
--- a/apps/webapp/app/v3/services/createOrgIntegration.server.ts
+++ b/apps/webapp/app/v3/services/createOrgIntegration.server.ts
@@ -1,10 +1,5 @@
 import { OrganizationIntegration } from "@trigger.dev/database";
 import { BaseService } from "./baseService.server";
-import { WebClient } from "@slack/web-api";
-import { env } from "~/env.server";
-import { $transaction } from "~/db.server";
-import { getSecretStore } from "~/services/secrets/secretStore.server";
-import { generateFriendlyId } from "../friendlyIdentifiers";
 import { OrgIntegrationRepository } from "~/models/orgIntegration.server";
 
 export class CreateOrgIntegrationService extends BaseService {