diff --git a/frontend/src/app/main/data/nitrate.cljs b/frontend/src/app/main/data/nitrate.cljs
index cd4328191e..9f89218084 100644
--- a/frontend/src/app/main/data/nitrate.cljs
+++ b/frontend/src/app/main/data/nitrate.cljs
@@ -13,6 +13,7 @@
    [app.util.i18n :refer [tr]]
    [app.util.storage :as storage]
    [beicon.v2.core :as rx]
+   [cuerdas.core :as str]
    [potok.v2.core :as ptk]))
 
 (def ^:private nitrate-entry-active-key ::nitrate-entry-active)
@@ -74,14 +75,48 @@
   (let [href (dm/str "/control-center/licenses/billing?callback=" (js/encodeURIComponent go-to-subscription-url))]
     (st/emit! (rt/nav-raw :href href))))
 
+(def nitrate-checkout-error-token "nitrate-checkout-error")
+(def nitrate-checkout-finish-error-token "nitrate-checkout-finish-error")
+(def nitrate-checkout-cancelled-token "nitrate-checkout-cancelled")
+
+(defn- append-query-param
+  [url key value]
+  (let [assoc-q  (fn [u]
+                   (update u :query
+                           (fn [q]
+                             (-> (u/query-string->map (or q ""))
+                                 (assoc (name key) value)
+                                 u/map->query-string))))
+        parsed   (u/uri url)
+        fragment (:fragment parsed)]
+    (if (str/blank? fragment)
+      (str (assoc-q parsed))
+      (-> parsed
+          (assoc :fragment (str (assoc-q (u/parse fragment))))
+          str))))
+
+(defn build-nitrate-callback-urls
+  "Build the success/error/cancel callback URLs from a base URL by appending
+  a `subscription` query param identifying the outcome."
+  [base-url]
+  (let [build (fn [token]
+                (append-query-param base-url :subscription token))]
+    {:success-callback      (build "subscribed-to-penpot-nitrate")
+     :error-callback        (build nitrate-checkout-error-token)
+     :finish-error-callback (build nitrate-checkout-finish-error-token)
+     :cancel-callback       (build nitrate-checkout-cancelled-token)}))
+
 (defn go-to-buy-nitrate-license
-  ([subscription]
-   (go-to-buy-nitrate-license subscription nil))
-  ([subscription callback]
-   (let [params (cond-> {:subscription subscription}
-                  callback (assoc :callback callback))
-         href   (dm/str "/control-center/licenses/start?" (u/map->query-string params))]
-     (st/emit! (rt/nav-raw :href href)))))
+  [subscription base-url]
+  (let [{:keys [success-callback error-callback finish-error-callback cancel-callback]}
+        (build-nitrate-callback-urls base-url)
+        params {:subscription subscription
+                :callback success-callback
+                :error_callback error-callback
+                :finish_error_callback finish-error-callback
+                :cancel_callback cancel-callback}
+        href   (dm/str "/control-center/licenses/start?" (u/map->query-string params))]
+    (st/emit! (rt/nav-raw :href href))))
 
 (defn fetch-connectivity
   []
diff --git a/frontend/src/app/main/ui/nitrate/nitrate_form.cljs b/frontend/src/app/main/ui/nitrate/nitrate_form.cljs
index 13143d5337..bb2bfecadd 100644
--- a/frontend/src/app/main/ui/nitrate/nitrate_form.cljs
+++ b/frontend/src/app/main/ui/nitrate/nitrate_form.cljs
@@ -40,7 +40,8 @@
         (mf/use-fn
          (mf/deps form)
          (fn []
-           (dnt/go-to-buy-nitrate-license (-> @form :clean-data :subscription name))))
+           (let [subscription (-> @form :clean-data :subscription name)]
+             (dnt/go-to-buy-nitrate-license subscription dnt/go-to-subscription-url))))
 
         on-activate-click
         (mf/use-fn
diff --git a/frontend/src/app/main/ui/settings/subscription.cljs b/frontend/src/app/main/ui/settings/subscription.cljs
index 51d5df31ba..972189e6b8 100644
--- a/frontend/src/app/main/ui/settings/subscription.cljs
+++ b/frontend/src/app/main/ui/settings/subscription.cljs
@@ -4,12 +4,12 @@
    [app.common.data.macros :as dm]
    [app.common.schema :as sm]
    [app.common.time :as ct]
-   [app.common.uri :as u]
    [app.config :as cf]
    [app.main.data.auth :as da]
    [app.main.data.event :as ev]
    [app.main.data.modal :as modal]
    [app.main.data.nitrate :as dnt]
+   [app.main.data.notifications :as ntf]
    [app.main.refs :as refs]
    [app.main.router :as rt]
    [app.main.store :as st]
@@ -39,7 +39,8 @@
            code-action
            editors
            recommended
-           show-button-cta]}]
+           show-button-cta
+           inline-error]}]
 
   (let [has-trial? (and cta-link-trial cta-text-trial)
         has-cta-with-icon? (and cta-link-with-icon cta-text-with-icon)
@@ -100,7 +101,9 @@
                              #(st/emit! (modal/show {:type :nitrate-code-activation})))}
         (if (= code-action :activate)
           (tr "subscription.settings.activate-by-code")
-          (tr "nitrate.subscription.settings.renew-with-code"))])]))
+          (tr "nitrate.subscription.settings.renew-with-code"))])
+     (when inline-error
+       [:p {:class (stl/css :inline-error)} inline-error])]))
 
 (defn- get-subscription-name [subscription-type subscribe-to-trial?]
   (if subscribe-to-trial?
@@ -399,6 +402,30 @@
             (= params-subscription "subscribed-to-penpot-enterprise")
             (= params-subscription "subscribed-to-penpot-nitrate"))
 
+        nitrate-toast-message
+        (condp = params-subscription
+          dnt/nitrate-checkout-finish-error-token (tr "subscription.error.nitrate.checkout-finish-failed")
+          dnt/nitrate-checkout-cancelled-token    (tr "subscription.error.nitrate.checkout-cancelled")
+          nil)
+
+        nitrate-toast-level
+        (cond
+          (= params-subscription dnt/nitrate-checkout-cancelled-token) :info
+          (some? nitrate-toast-message)                                :error)
+
+        show-nitrate-start-error?
+        (= params-subscription dnt/nitrate-checkout-error-token)
+
+        nitrate-start-error*
+        (mf/use-state false)
+
+        nitrate-start-error?
+        (deref nitrate-start-error*)
+
+        nitrate-start-error-message
+        (when nitrate-start-error?
+          (tr "subscription.error.nitrate.checkout-failed"))
+
         success-modal-is-trial?
         (-> route :params :query :trial)
 
@@ -485,10 +512,26 @@
     (mf/with-effect [authenticated?
                      show-subscription-success-modal?
                      show-trial-subscription-modal?
+                     show-nitrate-start-error?
                      success-modal-is-trial?
+                     nitrate-toast-message
+                     nitrate-toast-level
                      subscription]
       (when ^boolean authenticated?
+        (when ^boolean show-nitrate-start-error?
+          (reset! nitrate-start-error* true))
         (cond
+          (some? nitrate-toast-message)
+          (st/emit!
+           (ntf/show {:content nitrate-toast-message
+                      :type :toast
+                      :level nitrate-toast-level
+                      :timeout 7000})
+           (rt/nav :settings-subscription {} {::rt/replace true}))
+
+          ^boolean show-nitrate-start-error?
+          (st/emit! (rt/nav :settings-subscription {} {::rt/replace true}))
+
           ^boolean show-trial-subscription-modal?
 
           (st/emit!
@@ -676,7 +719,8 @@
                          :cta-text-with-icon (tr "subscription.settings.more-information")
                          :cta-link-with-icon go-to-pricing-page
                          :code-action :activate
-                         :show-button-cta (not nitrate-license)}])]]]))
+                         :show-button-cta (not nitrate-license)
+                         :inline-error nitrate-start-error-message}])]]]))
 
 
 (def ^:private schema:nitrate-form
@@ -703,13 +747,8 @@
         (mf/use-fn
          (mf/deps form)
          (fn []
-           (let [subscription (-> @form :clean-data :subscription name)
-                 return-url   (dm/str
-                               (rt/get-current-href)
-                               "?"
-                               (u/map->query-string
-                                {:subscription "subscribed-to-penpot-nitrate"}))]
-             (dnt/go-to-buy-nitrate-license subscription return-url))))]
+           (let [subscription (-> @form :clean-data :subscription name)]
+             (dnt/go-to-buy-nitrate-license subscription (rt/get-current-href)))))]
 
     [:div {:class (stl/css :modal-overlay)}
      [:div {:class (stl/css :modal-dialog)}
diff --git a/frontend/src/app/main/ui/settings/subscription.scss b/frontend/src/app/main/ui/settings/subscription.scss
index 09f1f8e370..436a512042 100644
--- a/frontend/src/app/main/ui/settings/subscription.scss
+++ b/frontend/src/app/main/ui/settings/subscription.scss
@@ -194,6 +194,13 @@
   margin-block-start: var(--sp-xl);
 }
 
+.inline-error {
+  @include t.use-typography("body-small");
+
+  color: var(--color-foreground-error);
+  margin-block: var(--sp-s) 0;
+}
+
 .modal-overlay {
   @extend %modal-overlay-base;
 }
diff --git a/frontend/test/frontend_tests/data/nitrate_test.cljs b/frontend/test/frontend_tests/data/nitrate_test.cljs
new file mode 100644
index 0000000000..cfe179b0ea
--- /dev/null
+++ b/frontend/test/frontend_tests/data/nitrate_test.cljs
@@ -0,0 +1,45 @@
+;; This Source Code Form is subject to the terms of the Mozilla Public
+;; License, v. 2.0. If a copy of the MPL was not distributed with this
+;; file, You can obtain one at http://mozilla.org/MPL/2.0/.
+;;
+;; Copyright (c) KALEIDOS INC
+
+(ns frontend-tests.data.nitrate-test
+  (:require
+   [app.common.uri :as u]
+   [app.main.data.nitrate :as dnt]
+   [cljs.test :as t :include-macros true]))
+
+(t/deftest build-nitrate-callback-urls-preserves-hash-query
+  (t/testing "appends subscription to an existing query inside the hash route"
+    (let [callbacks (dnt/build-nitrate-callback-urls
+                     "https://localhost:3449/#/dashboard/recent?team-id=e6666530-0216-81c8-8007-f17d6087b74f")]
+      (t/is (= "https://localhost:3449/#/dashboard/recent?team-id=e6666530-0216-81c8-8007-f17d6087b74f&subscription=subscribed-to-penpot-nitrate"
+               (:success-callback callbacks)))
+      (t/is (= "https://localhost:3449/#/dashboard/recent?team-id=e6666530-0216-81c8-8007-f17d6087b74f&subscription=nitrate-checkout-error"
+               (:error-callback callbacks)))
+      (t/is (= "https://localhost:3449/#/dashboard/recent?team-id=e6666530-0216-81c8-8007-f17d6087b74f&subscription=nitrate-checkout-finish-error"
+               (:finish-error-callback callbacks)))
+      (t/is (= "https://localhost:3449/#/dashboard/recent?team-id=e6666530-0216-81c8-8007-f17d6087b74f&subscription=nitrate-checkout-cancelled"
+               (:cancel-callback callbacks))))))
+
+(t/deftest build-nitrate-callback-urls-adds-hash-query-when-missing
+  (t/testing "adds a hash query when the route has no query string yet"
+    (let [callbacks (dnt/build-nitrate-callback-urls
+                     "https://localhost:3449/#/settings/subscriptions")]
+      (t/is (= "https://localhost:3449/#/settings/subscriptions?subscription=subscribed-to-penpot-nitrate"
+               (:success-callback callbacks))))))
+
+(t/deftest build-nitrate-callback-urls-adds-regular-query-without-hash
+  (t/testing "falls back to the regular URL query when there is no hash route"
+    (let [callbacks (dnt/build-nitrate-callback-urls
+                     "https://localhost:3449/control-center/licenses/billing?foo=bar")]
+      (t/is (= "https://localhost:3449/control-center/licenses/billing?foo=bar&subscription=subscribed-to-penpot-nitrate"
+               (:success-callback callbacks))))))
+
+(t/deftest build-nitrate-callback-urls-accepts-uri-object
+  (t/testing "accepts a URI object as base url (used by the nitrate-form modal)"
+    (let [callbacks (dnt/build-nitrate-callback-urls
+                     (u/uri "https://localhost:3449/#/settings/subscriptions"))]
+      (t/is (= "https://localhost:3449/#/settings/subscriptions?subscription=nitrate-checkout-error"
+               (:error-callback callbacks))))))
diff --git a/frontend/test/frontend_tests/runner.cljs b/frontend/test/frontend_tests/runner.cljs
index 5f9078f910..065ed3bf80 100644
--- a/frontend/test/frontend_tests/runner.cljs
+++ b/frontend/test/frontend_tests/runner.cljs
@@ -3,6 +3,7 @@
    [cljs.test :as t]
    [frontend-tests.basic-shapes-test]
    [frontend-tests.copy-as-svg-test]
+   [frontend-tests.data.nitrate-test]
    [frontend-tests.data.repo-test]
    [frontend-tests.data.uploads-test]
    [frontend-tests.data.viewer-test]
@@ -49,6 +50,7 @@
   (t/run-tests
    'frontend-tests.basic-shapes-test
    'frontend-tests.copy-as-svg-test
+   'frontend-tests.data.nitrate-test
    'frontend-tests.data.repo-test
    'frontend-tests.errors-test
    'frontend-tests.main-errors-test
diff --git a/frontend/translations/en.po b/frontend/translations/en.po
index 0c524f9777..6b14173adc 100644
--- a/frontend/translations/en.po
+++ b/frontend/translations/en.po
@@ -5166,6 +5166,15 @@ msgstr "Inviting people while on the Unlimited plan"
 msgid "subscription.dashboard.upgrade-plan.power-up"
 msgstr "Power up"
 
+msgid "subscription.error.nitrate.checkout-cancelled"
+msgstr "Payment was not completed. Try again whenever you're ready."
+
+msgid "subscription.error.nitrate.checkout-failed"
+msgstr "We couldn't start the checkout. Please try again. If the problem persists, contact us: support@penpot.app."
+
+msgid "subscription.error.nitrate.checkout-finish-failed"
+msgstr "We’re having trouble activating your subscription. Please try again. If the problem persists, contact us: support@penpot.app."
+
 #: src/app/main/ui/settings/sidebar.cljs:116, src/app/main/ui/settings/subscription.cljs:425, src/app/main/ui/settings/subscription.cljs:462
 msgid "subscription.labels"
 msgstr "Subscription"
diff --git a/frontend/translations/es.po b/frontend/translations/es.po
index 4bbf92126e..f81279149f 100644
--- a/frontend/translations/es.po
+++ b/frontend/translations/es.po
@@ -5084,6 +5084,15 @@ msgstr "Invita a personas mientras estás en el plan Unlimited"
 msgid "subscription.dashboard.upgrade-plan.power-up"
 msgstr "Mejora"
 
+msgid "subscription.error.nitrate.checkout-cancelled"
+msgstr "El pago no se completó. Inténtalo de nuevo cuando quieras."
+
+msgid "subscription.error.nitrate.checkout-failed"
+msgstr "No hemos podido iniciar el proceso de pago. Inténtalo de nuevo. Si el problema persiste, contáctanos: support@penpot.app."
+
+msgid "subscription.error.nitrate.checkout-finish-failed"
+msgstr "Estamos teniendo problemas para activar tu suscripción. Inténtalo de nuevo. Si el problema persiste, contáctanos: support@penpot.app."
+
 #: src/app/main/ui/settings/sidebar.cljs:116, src/app/main/ui/settings/subscription.cljs:425, src/app/main/ui/settings/subscription.cljs:462
 msgid "subscription.labels"
 msgstr "Suscripción"