diff --git a/apps/web/app/(ee)/api/cron/discount-codes/create/queue-batches/route.ts b/apps/web/app/(ee)/api/cron/discount-codes/create/queue-batches/route.ts
index cca8e0d2bab..cfb9461ed88 100644
--- a/apps/web/app/(ee)/api/cron/discount-codes/create/queue-batches/route.ts
+++ b/apps/web/app/(ee)/api/cron/discount-codes/create/queue-batches/route.ts
@@ -1,7 +1,7 @@
 import { CRON_BATCH_SIZE, qstash } from "@/lib/cron";
 import { enqueueBatchJobs } from "@/lib/cron/enqueue-batch-jobs";
 import { withCron } from "@/lib/cron/with-cron";
-import { isDiscountIntegrationNotAvailableError } from "@/lib/discounts/discount-error";
+import { isNonRecoverableDiscountError } from "@/lib/discounts/discount-error";
 import { getDiscountProvider } from "@/lib/discounts/discount-provider";
 import { prisma } from "@/lib/prisma";
 import { ACTIVE_ENROLLMENT_STATUSES } from "@/lib/zod/schemas/partners";
@@ -55,14 +55,12 @@ export const POST = withCron(async ({ rawBody }) => {
   const discountProvider = getDiscountProvider(discount.provider);
 
   try {
-    await discountProvider.assertDiscountIntegrationAvailable({
+    await discountProvider.assertDiscountIntegration({
       workspace: program.workspace,
     });
   } catch (error) {
-    if (isDiscountIntegrationNotAvailableError(error)) {
-      return logAndRespond(
-        `Workspace has not installed the ${discount.provider} integration. Skipping...`,
-      );
+    if (isNonRecoverableDiscountError(error)) {
+      return logAndRespond(error.message, { logLevel: "warn" });
     }
 
     throw error;
diff --git a/apps/web/app/(ee)/api/cron/discount-codes/create/route.ts b/apps/web/app/(ee)/api/cron/discount-codes/create/route.ts
index 0f231bfc00d..4888d4eafe4 100644
--- a/apps/web/app/(ee)/api/cron/discount-codes/create/route.ts
+++ b/apps/web/app/(ee)/api/cron/discount-codes/create/route.ts
@@ -1,6 +1,6 @@
 import { withCron } from "@/lib/cron/with-cron";
 import { createDiscountCode } from "@/lib/discounts/create-discount-code";
-import { isDiscountIntegrationNotAvailableError } from "@/lib/discounts/discount-error";
+import { isNonRecoverableDiscountError } from "@/lib/discounts/discount-error";
 import { prisma } from "@/lib/prisma";
 import * as z from "zod/v4";
 import { logAndRespond } from "../../utils";
@@ -90,20 +90,7 @@ export const POST = withCron(async ({ rawBody }) => {
       discount,
     });
   } catch (error) {
-    if (isDiscountIntegrationNotAvailableError(error)) {
-      return logAndRespond(
-        `Workspace has not installed the ${discount.provider} integration. Skipping...`,
-      );
-    }
-
-    // Eg: This application does not have the required permissions for this endpoint on account 'acct_xxx'.
-    // Having the 'read_write' scope would allow this request to continue.
-    if (
-      error instanceof Error &&
-      error.message.includes(
-        "This application does not have the required permissions",
-      )
-    ) {
+    if (isNonRecoverableDiscountError(error)) {
       return logAndRespond(error.message, { logLevel: "warn" });
     }
 
diff --git a/apps/web/app/(ee)/api/cron/discount-codes/disable/route.ts b/apps/web/app/(ee)/api/cron/discount-codes/disable/route.ts
index 7b4792d8c51..75ec424f80d 100644
--- a/apps/web/app/(ee)/api/cron/discount-codes/disable/route.ts
+++ b/apps/web/app/(ee)/api/cron/discount-codes/disable/route.ts
@@ -1,5 +1,5 @@
 import { withCron } from "@/lib/cron/with-cron";
-import { isDiscountIntegrationNotAvailableError } from "@/lib/discounts/discount-error";
+import { isNonRecoverableDiscountError } from "@/lib/discounts/discount-error";
 import { getDiscountProvider } from "@/lib/discounts/discount-provider";
 import { prisma } from "@/lib/prisma";
 import { DiscountProvider } from "@prisma/client";
@@ -37,8 +37,10 @@ export const POST = withCron(async ({ rawBody }) => {
       code,
     });
   } catch (error) {
-    if (isDiscountIntegrationNotAvailableError(error)) {
-      return logAndRespond(`Skipping ${code}: ${error.message}`);
+    if (isNonRecoverableDiscountError(error)) {
+      return logAndRespond(`Skipping ${code}: ${error.message}`, {
+        logLevel: "warn",
+      });
     }
 
     throw error;
diff --git a/apps/web/app/(ee)/api/cron/groups/remap-discount-codes/route.ts b/apps/web/app/(ee)/api/cron/groups/remap-discount-codes/route.ts
index e0a79faa107..a49f8dd9f68 100644
--- a/apps/web/app/(ee)/api/cron/groups/remap-discount-codes/route.ts
+++ b/apps/web/app/(ee)/api/cron/groups/remap-discount-codes/route.ts
@@ -1,7 +1,7 @@
 import { withCron } from "@/lib/cron/with-cron";
 import { createDiscountCode } from "@/lib/discounts/create-discount-code";
 import { deleteDiscountCodes } from "@/lib/discounts/delete-discount-code";
-import { isDiscountIntegrationNotAvailableError } from "@/lib/discounts/discount-error";
+import { isDiscountProviderError } from "@/lib/discounts/discount-error";
 import { isDiscountEquivalent } from "@/lib/discounts/is-discount-equivalent";
 import { prisma } from "@/lib/prisma";
 import { Discount, DiscountCode } from "@prisma/client";
@@ -164,13 +164,19 @@ export const POST = withCron(async ({ rawBody }) => {
             discount: group.discount,
           });
         } catch (error) {
-          if (isDiscountIntegrationNotAvailableError(error)) {
-            console.warn(
-              `Workspace has not installed the ${group.discount.provider} integration. Skipping remaining discount code creation for remap.`,
-            );
-            break;
+          if (isDiscountProviderError(error)) {
+            if (
+              error.providerCode === "INTEGRATION_NOT_AVAILABLE" ||
+              error.providerCode === "AUTH_EXPIRED" ||
+              error.providerCode === "PERMISSIONS_REQUIRED" ||
+              error.providerCode === "COUPON_NOT_FOUND"
+            ) {
+              console.warn(
+                `${error.message} Skipping remaining discount code creation for remap.`,
+              );
+              break;
+            }
           }
-
           throw error;
         }
       }
diff --git a/apps/web/lib/actions/partners/create-discount.ts b/apps/web/lib/actions/partners/create-discount.ts
index 81ed466f452..2dbcc188d62 100644
--- a/apps/web/lib/actions/partners/create-discount.ts
+++ b/apps/web/lib/actions/partners/create-discount.ts
@@ -67,7 +67,7 @@ export const createDiscountAction = authActionClient
         });
       }
     } else if (provider === DiscountProvider.shopify) {
-      await discountProvider.assertDiscountIntegrationAvailable({
+      await discountProvider.assertDiscountIntegration({
         workspace,
       });
     }
diff --git a/apps/web/lib/discounts/create-discount-code.ts b/apps/web/lib/discounts/create-discount-code.ts
index fd8e9153f34..d6d5b02c014 100644
--- a/apps/web/lib/discounts/create-discount-code.ts
+++ b/apps/web/lib/discounts/create-discount-code.ts
@@ -41,33 +41,12 @@ export async function createDiscountCode({
 
   const discountProvider = getDiscountProvider(discount.provider);
 
-  let externalDiscountCode: Awaited<
-    ReturnType<typeof discountProvider.createDiscountCode>
-  >;
-
-  try {
-    externalDiscountCode = await discountProvider.createDiscountCode({
-      workspace,
-      discount,
-      code: finalCode,
-      shouldRetry: code ? false : true,
-    });
-  } catch (error) {
-    const message = error?.raw?.message || error?.message || "";
-    const isDuplicateCode =
-      message.includes("already exists") ||
-      error?.code === "TAKEN" ||
-      error?.code === "DUPLICATE";
-
-    if (isDuplicateCode) {
-      throw new DubApiError({
-        code: "conflict",
-        message: `The discount code ${finalCode} is already in use. Please choose a different code.`,
-      });
-    }
-
-    throw error;
-  }
+  const externalDiscountCode = await discountProvider.createDiscountCode({
+    workspace,
+    discount,
+    code: finalCode,
+    shouldRetry: code ? false : true,
+  });
 
   try {
     return await prisma.discountCode.create({
diff --git a/apps/web/lib/discounts/discount-error.ts b/apps/web/lib/discounts/discount-error.ts
index 4b0a6b2ded0..5776a09ba10 100644
--- a/apps/web/lib/discounts/discount-error.ts
+++ b/apps/web/lib/discounts/discount-error.ts
@@ -1,15 +1,78 @@
 import { DubApiError } from "../api/errors";
 
-export class DiscountIntegrationNotAvailableError extends DubApiError {
-  constructor({ message }: { message: string }) {
-    super({ code: "bad_request", message });
-    this.name = "DiscountIntegrationNotAvailableError";
+export type DiscountProviderErrorCode =
+  | "INTEGRATION_NOT_AVAILABLE"
+  | "AUTH_EXPIRED"
+  | "DISCOUNT_ALREADY_EXISTS"
+  | "COUPON_NOT_FOUND"
+  | "PERMISSIONS_REQUIRED"
+  | "CREATE_FAILED";
+
+const API_CODE_BY_PROVIDER_CODE: Record<
+  DiscountProviderErrorCode,
+  "bad_request" | "conflict" | "internal_server_error"
+> = {
+  INTEGRATION_NOT_AVAILABLE: "bad_request",
+  AUTH_EXPIRED: "bad_request",
+  DISCOUNT_ALREADY_EXISTS: "conflict",
+  COUPON_NOT_FOUND: "bad_request",
+  PERMISSIONS_REQUIRED: "bad_request",
+  CREATE_FAILED: "internal_server_error",
+};
+
+function resolveDiscountProviderMessage(
+  provider: "stripe" | "shopify",
+  providerCode: DiscountProviderErrorCode,
+  message: string,
+): string {
+  if (providerCode === "INTEGRATION_NOT_AVAILABLE") {
+    return provider === "stripe"
+      ? "STRIPE_CONNECTION_REQUIRED: Your workspace isn't connected to Stripe yet. Please install the Dub Stripe app in settings to create a discount."
+      : "SHOPIFY_CONNECTION_REQUIRED: Your workspace isn't connected to Shopify yet. Please install the Dub Shopify app in settings to create a discount.";
+  }
+
+  if (providerCode === "AUTH_EXPIRED") {
+    return provider === "stripe"
+      ? "STRIPE_RECONNECT_REQUIRED: Your Stripe connection has expired or been revoked. Please reconnect the Dub Stripe app in settings."
+      : "SHOPIFY_RECONNECT_REQUIRED: Your Shopify connection has expired or been revoked. Please reconnect the Dub Shopify app in settings.";
+  }
+
+  if (providerCode === "PERMISSIONS_REQUIRED") {
+    return provider === "stripe"
+      ? "STRIPE_APP_UPGRADE_REQUIRED: Your connected Stripe account doesn't have the permissions needed to create discount codes. Please upgrade your Stripe integration in settings or reach out to our support team for help."
+      : "SHOPIFY_APP_UPGRADE_REQUIRED: Your connected Shopify store doesn't have permission to create discount codes. Please reinstall or upgrade the Dub Shopify app.";
+  }
+
+  return message;
+}
+
+export class DiscountProviderError extends DubApiError {
+  constructor(
+    public readonly provider: "stripe" | "shopify",
+    public readonly providerCode: DiscountProviderErrorCode,
+    message: string,
+  ) {
+    super({
+      code: API_CODE_BY_PROVIDER_CODE[providerCode],
+      message: resolveDiscountProviderMessage(provider, providerCode, message),
+    });
+    this.name = "DiscountProviderError";
     Object.setPrototypeOf(this, new.target.prototype);
   }
+
+  get isRecoverable() {
+    return this.providerCode === "CREATE_FAILED";
+  }
+}
+
+export function isDiscountProviderError(
+  error: unknown,
+): error is DiscountProviderError {
+  return error instanceof DiscountProviderError;
 }
 
-export function isDiscountIntegrationNotAvailableError(
+export function isNonRecoverableDiscountError(
   error: unknown,
-): error is DiscountIntegrationNotAvailableError {
-  return error instanceof DiscountIntegrationNotAvailableError;
+): error is DiscountProviderError {
+  return isDiscountProviderError(error) && !error.isRecoverable;
 }
diff --git a/apps/web/lib/discounts/discount-provider-shopify.ts b/apps/web/lib/discounts/discount-provider-shopify.ts
index 373a17998e4..4f86f5be437 100644
--- a/apps/web/lib/discounts/discount-provider-shopify.ts
+++ b/apps/web/lib/discounts/discount-provider-shopify.ts
@@ -7,7 +7,7 @@ import {
   shopifyAdminGraphql,
 } from "../integrations/shopify/admin-graphql";
 import { integrationCredentialsSchema } from "../integrations/shopify/schema";
-import { DiscountIntegrationNotAvailableError } from "./discount-error";
+import { DiscountProviderError } from "./discount-error";
 
 interface ShopifyDiscountCodeBasicCreate {
   codeDiscountNode: {
@@ -38,10 +38,11 @@ async function requireInstalledIntegration(
   workspace: Pick<Project, "id" | "shopifyStoreId">,
 ) {
   if (!workspace.shopifyStoreId) {
-    throw new DiscountIntegrationNotAvailableError({
-      message:
-        "SHOPIFY_CONNECTION_REQUIRED: Your workspace isn't connected to Shopify yet. Please install the Dub Shopify app in settings to create a discount.",
-    });
+    throw new DiscountProviderError(
+      "shopify",
+      "INTEGRATION_NOT_AVAILABLE",
+      "SHOPIFY_CONNECTION_REQUIRED: Your workspace isn't connected to Shopify yet. Please install the Dub Shopify app in settings to create a discount.",
+    );
   }
 
   const installation = await prisma.installedIntegration.findFirst({
@@ -52,10 +53,11 @@ async function requireInstalledIntegration(
   });
 
   if (!installation) {
-    throw new DiscountIntegrationNotAvailableError({
-      message:
-        "SHOPIFY_CONNECTION_REQUIRED: Your workspace isn't connected to Shopify yet. Please install the Dub Shopify app in settings to create a discount.",
-    });
+    throw new DiscountProviderError(
+      "shopify",
+      "INTEGRATION_NOT_AVAILABLE",
+      "SHOPIFY_CONNECTION_REQUIRED: Your workspace isn't connected to Shopify yet. Please install the Dub Shopify app in settings to create a discount.",
+    );
   }
 
   let credentials = integrationCredentialsSchema.parse(
@@ -63,10 +65,11 @@ async function requireInstalledIntegration(
   );
 
   if (!credentials?.scope?.includes("write_discounts")) {
-    throw new DiscountIntegrationNotAvailableError({
-      message:
-        "SHOPIFY_APP_UPGRADE_REQUIRED: Your connected Shopify store doesn't have permission to create discount codes. Please reinstall or upgrade the Dub Shopify app.",
-    });
+    throw new DiscountProviderError(
+      "shopify",
+      "PERMISSIONS_REQUIRED",
+      "SHOPIFY_APP_UPGRADE_REQUIRED: Your connected Shopify store doesn't have permission to create discount codes. Please reinstall or upgrade the Dub Shopify app.",
+    );
   }
 
   return {
@@ -80,6 +83,15 @@ async function requireInstalledIntegration(
   };
 }
 
+function throwIfShopifyUnauthorized(error: unknown): void {
+  if (
+    error instanceof ShopifyAdminGraphqlError &&
+    error.code === "unauthorized"
+  ) {
+    throw new DiscountProviderError("shopify", "AUTH_EXPIRED", error.message);
+  }
+}
+
 function createShopifyDiscountProvider() {
   const getCoupon = async () => {
     throw new Error("Shopify does not this method.");
@@ -187,7 +199,7 @@ function createShopifyDiscountProvider() {
         if (!codeDiscountNode) {
           throw new ShopifyAdminGraphqlError(
             "no_node_returned",
-            "Shopify did not return a discount code node.",
+            "Shopify did not return a discount code. Please try again.",
           );
         }
 
@@ -199,27 +211,64 @@ function createShopifyDiscountProvider() {
           error instanceof ShopifyAdminGraphqlError &&
           (error.code === "TAKEN" || error.code === "DUPLICATE");
 
-        if (!isDuplicate || !shouldRetry) {
-          throw error;
-        }
+        if (isDuplicate) {
+          if (!shouldRetry) {
+            throw new DiscountProviderError(
+              "shopify",
+              "DISCOUNT_ALREADY_EXISTS",
+              `The discount code ${currentCode} is already in use. Please choose a different code.`,
+            );
+          }
 
-        attempt++;
+          attempt++;
 
-        if (attempt >= MAX_ATTEMPTS) {
-          throw error;
+          if (attempt >= MAX_ATTEMPTS) {
+            throw new DiscountProviderError(
+              "shopify",
+              "CREATE_FAILED",
+              `Failed to create a unique discount code after ${MAX_ATTEMPTS} attempts. Please try again.`,
+            );
+          }
+
+          const newCode = `${currentCode}${nanoid(2)}`;
+
+          console.warn(
+            `Discount code "${currentCode}" already exists in Shopify. Retrying with "${newCode}" (attempt ${attempt}/${MAX_ATTEMPTS}).`,
+          );
+
+          currentCode = newCode;
+          continue;
         }
 
-        const newCode = `${currentCode}${nanoid(2)}`;
+        if (error instanceof ShopifyAdminGraphqlError) {
+          throwIfShopifyUnauthorized(error);
+
+          throw new DiscountProviderError(
+            "shopify",
+            "CREATE_FAILED",
+            error.code === "no_node_returned"
+              ? "Shopify did not return a discount code. Please try again."
+              : error.code === "http_error" || error.code === "graphql_error"
+                ? `Unable to create the discount code in Shopify. ${error.message}`
+                : error.message,
+          );
+        }
 
-        console.warn(
-          `Discount code "${currentCode}" already exists in Shopify. Retrying with "${newCode}" (attempt ${attempt}/${MAX_ATTEMPTS}).`,
+        throw new DiscountProviderError(
+          "shopify",
+          "CREATE_FAILED",
+          error instanceof Error
+            ? error.message
+            : "Failed to create Shopify discount code.",
         );
-
-        currentCode = newCode;
       }
     }
 
-    throw new Error("Failed to create Shopify discount code.");
+    throw new DiscountProviderError(
+      "shopify",
+      "CREATE_FAILED",
+      "Failed to create Shopify discount code.",
+    );
   };
 
   const disableDiscountCode = async ({
@@ -231,68 +280,76 @@ function createShopifyDiscountProvider() {
   }) => {
     const { credentials } = await requireInstalledIntegration(workspace);
 
-    const lookup = await shopifyAdminGraphql<{
-      codeDiscountNodeByCode: { id: string } | null;
-    }>({
-      shopifyStoreId: workspace.shopifyStoreId!,
-      accessToken: credentials.accessToken!,
-      query: /* GraphQL */ `
-        query CodeDiscountNodeByCode($code: String!) {
-          codeDiscountNodeByCode(code: $code) {
-            id
+    try {
+      const lookup = await shopifyAdminGraphql<{
+        codeDiscountNodeByCode: { id: string } | null;
+      }>({
+        shopifyStoreId: workspace.shopifyStoreId!,
+        accessToken: credentials.accessToken!,
+        query: /* GraphQL */ `
+          query CodeDiscountNodeByCode($code: String!) {
+            codeDiscountNodeByCode(code: $code) {
+              id
+            }
           }
-        }
-      `,
-      variables: { code },
-    });
+        `,
+        variables: { code },
+      });
 
-    const id = lookup.codeDiscountNodeByCode?.id;
+      const id = lookup.codeDiscountNodeByCode?.id;
 
-    if (!id) {
-      console.error(
-        `Shopify discount code ${code} not found (shopifyStoreId=${workspace.shopifyStoreId!}).`,
-      );
-      return;
-    }
+      if (!id) {
+        console.error(
+          `Shopify discount code ${code} not found (shopifyStoreId=${workspace.shopifyStoreId!}).`,
+        );
+        return;
+      }
 
-    const data = await shopifyAdminGraphql<{
-      discountCodeDelete: ShopifyDiscountCodeDelete;
-    }>({
-      shopifyStoreId: workspace.shopifyStoreId!,
-      accessToken: credentials.accessToken!,
-      query: /* GraphQL */ `
-        mutation DiscountCodeDelete($id: ID!) {
-          discountCodeDelete(id: $id) {
-            deletedCodeDiscountId
-            userErrors {
-              field
-              message
-              code
+      const data = await shopifyAdminGraphql<{
+        discountCodeDelete: ShopifyDiscountCodeDelete;
+      }>({
+        shopifyStoreId: workspace.shopifyStoreId!,
+        accessToken: credentials.accessToken!,
+        query: /* GraphQL */ `
+          mutation DiscountCodeDelete($id: ID!) {
+            discountCodeDelete(id: $id) {
+              deletedCodeDiscountId
+              userErrors {
+                field
+                message
+                code
+              }
             }
           }
-        }
-      `,
-      variables: { id },
-    });
+        `,
+        variables: { id },
+      });
 
-    const { userErrors } = data.discountCodeDelete;
+      const { userErrors } = data.discountCodeDelete;
 
-    if (userErrors.length > 0) {
-      throw new ShopifyAdminGraphqlError(
-        userErrors[0].code,
-        userErrors[0].message,
-        userErrors,
-      );
-    }
+      if (userErrors.length > 0) {
+        throw new ShopifyAdminGraphqlError(
+          userErrors[0].code,
+          userErrors[0].message,
+          userErrors,
+        );
+      }
 
-    console.info(
-      `Deleted Shopify discount code ${code} (id=${id}, shopifyStoreId=${workspace.shopifyStoreId}).`,
-    );
+      console.info(
+        `Deleted Shopify discount code ${code} (id=${id}, shopifyStoreId=${workspace.shopifyStoreId}).`,
+      );
 
-    return { id, code };
+      return {
+        id,
+        code,
+      };
+    } catch (error) {
+      throwIfShopifyUnauthorized(error);
+      throw error;
+    }
   };
 
-  const assertDiscountIntegrationAvailable = async ({
+  const assertDiscountIntegration = async ({
     workspace,
   }: {
     workspace: Pick<Project, "id" | "stripeConnectId" | "shopifyStoreId">;
@@ -305,7 +362,7 @@ function createShopifyDiscountProvider() {
     createCoupon,
     createDiscountCode,
     disableDiscountCode,
-    assertDiscountIntegrationAvailable,
+    assertDiscountIntegration,
   };
 }
 
diff --git a/apps/web/lib/discounts/discount-provider-stripe.ts b/apps/web/lib/discounts/discount-provider-stripe.ts
index fe4022563eb..7910499fa36 100644
--- a/apps/web/lib/discounts/discount-provider-stripe.ts
+++ b/apps/web/lib/discounts/discount-provider-stripe.ts
@@ -12,7 +12,7 @@ import {
 } from "../stripe/coupon-discount-converter";
 import { DiscountProps } from "../types";
 import { createDiscountSchema } from "../zod/schemas/discount";
-import { DiscountIntegrationNotAvailableError } from "./discount-error";
+import { DiscountProviderError } from "./discount-error";
 
 const MAX_ATTEMPTS = 3;
 
@@ -20,10 +20,11 @@ async function requireInstalledIntegration(
   workspace: Pick<Project, "id" | "stripeConnectId">,
 ) {
   if (!workspace.stripeConnectId) {
-    throw new DiscountIntegrationNotAvailableError({
-      message:
-        "STRIPE_CONNECTION_REQUIRED: Your workspace isn't connected to Stripe yet. Please install the Dub Stripe app in settings to create a discount.",
-    });
+    throw new DiscountProviderError(
+      "stripe",
+      "INTEGRATION_NOT_AVAILABLE",
+      "STRIPE_CONNECTION_REQUIRED: Your workspace isn't connected to Stripe yet. Please install the Dub Stripe app in settings to create a discount.",
+    );
   }
 
   const installation = await prisma.installedIntegration.findFirst({
@@ -34,10 +35,11 @@ async function requireInstalledIntegration(
   });
 
   if (!installation) {
-    throw new DiscountIntegrationNotAvailableError({
-      message:
-        "STRIPE_CONNECTION_REQUIRED: Your workspace isn't connected to Stripe yet. Please install the Dub Stripe app in settings to create a discount.",
-    });
+    throw new DiscountProviderError(
+      "stripe",
+      "INTEGRATION_NOT_AVAILABLE",
+      "STRIPE_CONNECTION_REQUIRED: Your workspace isn't connected to Stripe yet. Please install the Dub Stripe app in settings to create a discount.",
+    );
   }
 
   const settings = stripeIntegrationSettingsSchema.parse(
@@ -50,6 +52,23 @@ async function requireInstalledIntegration(
   };
 }
 
+function isStripePermissionsError(error: {
+  code?: string;
+  message?: string;
+  raw?: { message?: string };
+}): boolean {
+  const errorMessage = error.raw?.message || error.message;
+
+  return (
+    error.code === "more_permissions_required_for_application" ||
+    Boolean(
+      errorMessage?.includes(
+        "This application does not have the required permissions",
+      ),
+    )
+  );
+}
+
 function createStripeDiscountProvider() {
   const getCoupon = async ({
     couponId,
@@ -148,9 +167,15 @@ function createStripeDiscountProvider() {
     });
 
     if (!discount.couponId) {
-      throw new Error(`couponId not found for discount ${discount.id}.`);
+      throw new DiscountProviderError(
+        "stripe",
+        "COUPON_NOT_FOUND",
+        "The coupon ID for this discount was not found. Please check the discount configuration and try again.",
+      );
     }
 
+    const couponId = discount.couponId;
+
     let attempt = 0;
     let currentCode = code;
 
@@ -158,7 +183,7 @@ function createStripeDiscountProvider() {
       try {
         return await stripeApp.promotionCodes.create(
           {
-            coupon: discount.couponId,
+            coupon: couponId,
             code: currentCode.toUpperCase(),
             restrictions: {
               first_time_transaction:
@@ -173,31 +198,64 @@ function createStripeDiscountProvider() {
         const errorMessage = error.raw?.message || error.message;
         const isDuplicateError = errorMessage?.includes("already exists");
 
-        if (!isDuplicateError) {
-          throw error;
+        if (isDuplicateError) {
+          if (!shouldRetry) {
+            throw new DiscountProviderError(
+              "stripe",
+              "DISCOUNT_ALREADY_EXISTS",
+              `The discount code ${currentCode} is already in use. Please choose a different code.`,
+            );
+          }
+
+          attempt++;
+
+          if (attempt >= MAX_ATTEMPTS) {
+            throw new DiscountProviderError(
+              "stripe",
+              "CREATE_FAILED",
+              `Failed to create a unique discount code after ${MAX_ATTEMPTS} attempts. Please try again.`,
+            );
+          }
+
+          const newCode = `${currentCode}${nanoid(2)}`;
+
+          console.warn(
+            `Discount code "${currentCode}" already exists. Retrying with "${newCode}" (attempt ${attempt}/${MAX_ATTEMPTS}).`,
+          );
+
+          currentCode = newCode;
+          continue;
         }
 
-        if (!shouldRetry) {
-          throw error;
+        if (isStripePermissionsError(error)) {
+          throw new DiscountProviderError(
+            "stripe",
+            "PERMISSIONS_REQUIRED",
+            errorMessage,
+          );
         }
 
-        attempt++;
-
-        if (attempt >= MAX_ATTEMPTS) {
-          throw error;
+        if (error.code === "resource_missing") {
+          throw new DiscountProviderError(
+            "stripe",
+            "COUPON_NOT_FOUND",
+            `The coupon ID you provided (${couponId}) was not found in your Stripe account. Please check the coupon ID and try again.`,
+          );
         }
 
-        const newCode = `${currentCode}${nanoid(2)}`;
-
-        console.warn(
-          `Discount code "${currentCode}" already exists. Retrying with "${newCode}" (attempt ${attempt}/${MAX_ATTEMPTS}).`,
+        throw new DiscountProviderError(
+          "stripe",
+          "CREATE_FAILED",
+          errorMessage || "Failed to create Stripe discount code.",
         );
-
-        currentCode = newCode;
       }
     }
 
-    throw new Error("Failed to create Stripe discount code.");
+    throw new DiscountProviderError(
+      "stripe",
+      "CREATE_FAILED",
+      "Failed to create Stripe discount code.",
+    );
   };
 
   const disableDiscountCode = async ({
@@ -213,43 +271,55 @@ function createStripeDiscountProvider() {
       mode: settings.stripeMode,
     });
 
-    const promotionCodes = await stripeApp.promotionCodes.list(
-      {
-        code,
-        limit: 1,
-      },
-      {
-        stripeAccount: workspace.stripeConnectId!,
-      },
-    );
-
-    if (promotionCodes.data.length === 0) {
-      console.error(
-        `Stripe promotion code ${code} not found (stripeConnectId=${workspace.stripeConnectId}).`,
+    try {
+      const promotionCodes = await stripeApp.promotionCodes.list(
+        {
+          code,
+          limit: 1,
+        },
+        {
+          stripeAccount: workspace.stripeConnectId!,
+        },
       );
-      return;
-    }
 
-    const promotionCode = promotionCodes.data[0];
+      if (promotionCodes.data.length === 0) {
+        console.error(
+          `Stripe promotion code ${code} not found (stripeConnectId=${workspace.stripeConnectId}).`,
+        );
+        return;
+      }
 
-    await stripeApp.promotionCodes.update(
-      promotionCode.id,
-      {
-        active: false,
-      },
-      {
-        stripeAccount: workspace.stripeConnectId!,
-      },
-    );
+      const promotionCode = promotionCodes.data[0];
 
-    console.info(
-      `Disabled Stripe promotion code ${promotionCode.code} (id=${promotionCode.id}, stripeConnectId=${workspace.stripeConnectId}).`,
-    );
+      await stripeApp.promotionCodes.update(
+        promotionCode.id,
+        {
+          active: false,
+        },
+        {
+          stripeAccount: workspace.stripeConnectId!,
+        },
+      );
+
+      console.info(
+        `Disabled Stripe promotion code ${promotionCode.code} (id=${promotionCode.id}, stripeConnectId=${workspace.stripeConnectId}).`,
+      );
 
-    return promotionCode;
+      return promotionCode;
+    } catch (error: any) {
+      if (isStripePermissionsError(error)) {
+        throw new DiscountProviderError(
+          "stripe",
+          "PERMISSIONS_REQUIRED",
+          error.raw?.message || error.message,
+        );
+      }
+
+      throw error;
+    }
   };
 
-  const assertDiscountIntegrationAvailable = async ({
+  const assertDiscountIntegration = async ({
     workspace,
   }: {
     workspace: Pick<Project, "id" | "stripeConnectId" | "shopifyStoreId">;
@@ -262,7 +332,7 @@ function createStripeDiscountProvider() {
     createCoupon,
     createDiscountCode,
     disableDiscountCode,
-    assertDiscountIntegrationAvailable,
+    assertDiscountIntegration,
   };
 }
 
diff --git a/apps/web/ui/partners/constants.ts b/apps/web/ui/partners/constants.ts
index a59782af0dc..8fd7b5607aa 100644
--- a/apps/web/ui/partners/constants.ts
+++ b/apps/web/ui/partners/constants.ts
@@ -17,9 +17,19 @@ export const ERROR_MAP: Record<
     ctaLabel: "Install Shopify app",
     ctaUrl: "https://apps.shopify.com/dub-conversion-tracking",
   },
+  SHOPIFY_RECONNECT_REQUIRED: {
+    title: "Shopify reconnection required",
+    ctaLabel: "Reconnect Shopify app",
+    ctaUrl: "https://apps.shopify.com/dub-conversion-tracking",
+  },
   SHOPIFY_APP_UPGRADE_REQUIRED: {
     title: "Shopify app upgrade required",
     ctaLabel: "Review permissions",
     ctaUrl: "https://apps.shopify.com/dub-conversion-tracking",
   },
+  STRIPE_RECONNECT_REQUIRED: {
+    title: "Stripe reconnection required",
+    ctaLabel: "Reconnect Stripe app",
+    ctaUrl: "https://marketplace.stripe.com/apps/dub-conversions",
+  },
 };