diff --git a/app/services/task_service/push_external.rb b/app/services/task_service/push_external.rb
index fcbb34c66..dc21fa1dc 100644
--- a/app/services/task_service/push_external.rb
+++ b/app/services/task_service/push_external.rb
@@ -9,17 +9,24 @@ def initialize(zip:, account_link:)
     end
 
     def execute
-      body = @zip.string
-      begin
-        response = connection.post {|request| request_parameters(request, body) }
-        response.success? ? nil : response.body
-      rescue StandardError => e
-        e
-      end
+      response = connection.post {|request| request_parameters(request, @zip.string) }
+      return nil if response.success?
+      return I18n.t('tasks.export_external_confirm.not_authorized', account_link: @account_link.name) if response.status == 401
+
+      handle_error(message: response.body)
+    rescue Faraday::ServerError => e
+      handle_error(error: e, message: I18n.t('tasks.export_external_confirm.server_error', account_link: @account_link.name))
+    rescue StandardError => e
+      handle_error(error: e)
     end
 
     private
 
+    def handle_error(message: nil, error: nil)
+      Sentry.capture_exception(error) if error.present?
+      ERB::Util.html_escape(message || error.to_s)
+    end
+
     def request_parameters(request, body)
       request.tap do |req|
         req.headers['Content-Type'] = 'application/zip'
@@ -31,6 +38,9 @@ def request_parameters(request, body)
 
     def connection
       Faraday.new(url: @account_link.push_url) do |faraday|
+        faraday.options[:open_timeout] = 5
+        faraday.options[:timeout] = 5
+
         faraday.adapter Faraday.default_adapter
       end
     end
diff --git a/config/locales/de/controllers/tasks.yml b/config/locales/de/controllers/tasks.yml
index fe3b551c0..f2c025a2d 100644
--- a/config/locales/de/controllers/tasks.yml
+++ b/config/locales/de/controllers/tasks.yml
@@ -7,7 +7,9 @@ de:
     duplicate:
       error_alert: Die Aufgabe konnte nicht dupliziert werden.
     export_external_confirm:
-      error: 'Der Export der Aufgabe (%{title}) ist fehlgeschlagen. <br> Fehler: %{error}'
+      error: 'Der Export der Aufgabe (%{title}) ist fehlgeschlagen. <br><br> Fehler: %{error}'
+      not_authorized: Die Autorisierung mit "%{account_link}" konnte nicht hergestellt werden. Ist der API-Schlüssel korrekt?
+      server_error: Verbindung zu %{account_link} fehlgeschlagen. Gegenseite nicht erreichbar.
       success: Aufgabe (%{title}) erfolgreich exportiert.
     import:
       internal_error: Beim Import dieser Aufgabe ist auf CodeHarbor ein interner Fehler aufgetreten.
diff --git a/config/locales/en/controllers/tasks.yml b/config/locales/en/controllers/tasks.yml
index b3dc07df5..7db64d2a8 100644
--- a/config/locales/en/controllers/tasks.yml
+++ b/config/locales/en/controllers/tasks.yml
@@ -7,7 +7,9 @@ en:
     duplicate:
       error_alert: Task could not be duplicated
     export_external_confirm:
-      error: 'Export of task (%{title}) failed. <br> Error: %{error}'
+      error: 'Export of task (%{title}) failed. <br><br> Error: %{error}'
+      not_authorized: Authorization with could not be established with "%{account_link}". Is the API Key correct?
+      server_error: Connection to %{account_link} failed. Remote host unreachable.
       success: Task (%{title}) successfully exported.
     import:
       internal_error: An internal error occurred on CodeHarbor while importing the exercise.
diff --git a/spec/services/task_service/push_external_spec.rb b/spec/services/task_service/push_external_spec.rb
index d6b281998..9e3d69003 100644
--- a/spec/services/task_service/push_external_spec.rb
+++ b/spec/services/task_service/push_external_spec.rb
@@ -51,7 +51,38 @@
         let(:status) { 500 }
         let(:response) { 'an error occured' }
 
-        it { is_expected.to be response }
+        it { is_expected.to eql response }
+
+        context 'when response contains problematic characters' do
+          let(:response) { 'an <error> occurred' }
+
+          it { is_expected.to eql 'an &lt;error&gt; occurred' }
+        end
+      end
+
+      context 'when response status is 401' do
+        let(:status) { 401 }
+        let(:response) { I18n.t('tasks.export_external_confirm.not_authorized', account_link: account_link.name) }
+
+        it { is_expected.to eq response }
+      end
+
+      context 'when faraday throws an error' do
+        let(:connection) { instance_double(Faraday::Connection) }
+        let(:error) { Faraday::ServerError }
+
+        before do
+          allow(Faraday).to receive(:new).and_return(connection)
+          allow(connection).to receive(:post).and_raise(error)
+        end
+
+        it { is_expected.to eql I18n.t('tasks.export_external_confirm.server_error', account_link: account_link.name) }
+
+        context 'when another error occurs' do
+          let(:error) { 'another error' }
+
+          it { is_expected.to eql 'another error' }
+        end
       end
     end