diff --git a/client/src/components/esignature-custom-document/esignature-custom-document.component.jsx b/client/src/components/esignature-custom-document/esignature-custom-document.component.jsx
index b0c09aeea..59d5cab67 100644
--- a/client/src/components/esignature-custom-document/esignature-custom-document.component.jsx
+++ b/client/src/components/esignature-custom-document/esignature-custom-document.component.jsx
@@ -8,6 +8,7 @@ import { createStructuredSelector } from "reselect";
 import { useNotification } from "../../contexts/Notifications/notificationContext.jsx";
 import { setModalContext } from "../../redux/modals/modals.actions";
 import { selectBodyshop } from "../../redux/user/user.selectors";
+import { hasDocumensoApiKey } from "../../utils/esignature.js";
 
 const mapStateToProps = createStructuredSelector({
   bodyshop: selectBodyshop
@@ -28,6 +29,10 @@ export function EsignatureCustomDocument({ bodyshop, jobId, setEsignatureContext
   const notification = useNotification();
   const { t } = useTranslation();
 
+  if (!hasDocumensoApiKey(bodyshop)) {
+    return null;
+  }
+
   const uploadCustomDocument = async ({ file, onError, onSuccess }) => {
     const formData = new FormData();
     formData.append("document", file);
diff --git a/client/src/components/esignature-modal/esignature-modal.container.jsx b/client/src/components/esignature-modal/esignature-modal.container.jsx
index 48232d258..09ce49ad6 100644
--- a/client/src/components/esignature-modal/esignature-modal.container.jsx
+++ b/client/src/components/esignature-modal/esignature-modal.container.jsx
@@ -9,6 +9,7 @@ import { selectEsignature } from "../../redux/modals/modals.selectors";
 import { selectBodyshop, selectCurrentUser } from "../../redux/user/user.selectors";
 import { useState } from "react";
 import InstanceRenderManager from "../../utils/instanceRenderMgr";
+import { hasDocumensoApiKey } from "../../utils/esignature.js";
 
 const mapStateToProps = createStructuredSelector({
   esignatureModal: selectEsignature,
@@ -25,6 +26,11 @@ export function EsignatureModalContainer({ esignatureModal, toggleModalVisible,
   const { open, context } = esignatureModal;
   const { token, envelopeId, documentId, jobid } = context;
   const [distributing, setDistributing] = useState(false);
+
+  if (!hasDocumensoApiKey(bodyshop)) {
+    return null;
+  }
+
   return (
     <Modal
       open={open}
diff --git a/client/src/components/job-audit-trail/job-audit-trail.component.jsx b/client/src/components/job-audit-trail/job-audit-trail.component.jsx
index 481509763..e29baafb5 100644
--- a/client/src/components/job-audit-trail/job-audit-trail.component.jsx
+++ b/client/src/components/job-audit-trail/job-audit-trail.component.jsx
@@ -14,6 +14,7 @@ import { HasFeatureAccess } from "../feature-wrapper/feature-wrapper.component";
 import UpsellComponent, { upsellEnum } from "../upsell/upsell.component";
 import axios from "axios";
 import { useNotification } from "../../contexts/Notifications/notificationContext";
+import { hasDocumensoApiKey } from "../../utils/esignature.js";
 
 const mapStateToProps = createStructuredSelector({
   bodyshop: selectBodyshop
@@ -26,6 +27,7 @@ export default connect(mapStateToProps, mapDispatchToProps)(JobAuditTrail);
 export function JobAuditTrail({ bodyshop, jobId }) {
   const { t } = useTranslation();
   const notification = useNotification();
+  const esignatureEnabled = hasDocumensoApiKey(bodyshop);
   const { loading, data, refetch } = useQuery(QUERY_AUDIT_TRAIL, {
     variables: { jobid: jobId },
     skip: !jobId,
@@ -326,18 +328,20 @@ export function JobAuditTrail({ bodyshop, jobId }) {
           />
         </Card>
       </Col>
-      <Col span={24}>
-        <Card title={t("jobs.labels.esignatures")}>
-          <ResponsiveTable
-            loading={loading}
-            columns={esigColumns}
-            mobileColumnKeys={["title", "status"]}
-            rowKey="id"
-            scroll={{ x: true }}
-            dataSource={data ? data.esignature_documents : []}
-          />
-        </Card>
-      </Col>
+      {esignatureEnabled && (
+        <Col span={24}>
+          <Card title={t("jobs.labels.esignatures")}>
+            <ResponsiveTable
+              loading={loading}
+              columns={esigColumns}
+              mobileColumnKeys={["title", "status"]}
+              rowKey="id"
+              scroll={{ x: true }}
+              dataSource={data ? data.esignature_documents : []}
+            />
+          </Card>
+        </Col>
+      )}
     </Row>
   );
 }
diff --git a/client/src/components/notification-settings/column-header-checkbox.component.jsx b/client/src/components/notification-settings/column-header-checkbox.component.jsx
index 5a857921e..1efdfe420 100644
--- a/client/src/components/notification-settings/column-header-checkbox.component.jsx
+++ b/client/src/components/notification-settings/column-header-checkbox.component.jsx
@@ -1,4 +1,3 @@
-import { notificationScenarios } from "../../utils/jobNotificationScenarios.js";
 import { Checkbox, Form } from "antd";
 import { useTranslation } from "react-i18next";
 import PropTypes from "prop-types";
@@ -9,18 +8,18 @@ import PropTypes from "prop-types";
  * @param form
  * @param disabled
  * @param onHeaderChange
+ * @param scenarioKeys
  * @returns {JSX.Element}
  * @constructor
  */
-const ColumnHeaderCheckbox = ({ channel, form, disabled = false, onHeaderChange }) => {
+const ColumnHeaderCheckbox = ({ channel, form, disabled = false, onHeaderChange, scenarioKeys }) => {
   const { t } = useTranslation();
 
   // Subscribe to all form values so that this component re-renders on changes.
   const formValues = Form.useWatch([], form) || {};
 
   // Determine if all scenarios for this channel are checked.
-  const allChecked =
-    notificationScenarios.length > 0 && notificationScenarios.every((scenario) => formValues[scenario]?.[channel]);
+  const allChecked = scenarioKeys.length > 0 && scenarioKeys.every((scenario) => formValues[scenario]?.[channel]);
 
   const onChange = (e) => {
     const checked = e.target.checked;
@@ -28,7 +27,7 @@ const ColumnHeaderCheckbox = ({ channel, form, disabled = false, onHeaderChange
     const currentValues = form.getFieldsValue();
     // Update each scenario for this channel.
     const newValues = { ...currentValues };
-    notificationScenarios.forEach((scenario) => {
+    scenarioKeys.forEach((scenario) => {
       newValues[scenario] = { ...newValues[scenario], [channel]: checked };
     });
     // Update form values.
@@ -50,7 +49,8 @@ ColumnHeaderCheckbox.propTypes = {
   channel: PropTypes.oneOf(["app", "email", "fcm"]).isRequired,
   form: PropTypes.object.isRequired,
   disabled: PropTypes.bool,
-  onHeaderChange: PropTypes.func
+  onHeaderChange: PropTypes.func,
+  scenarioKeys: PropTypes.arrayOf(PropTypes.string).isRequired
 };
 
 export default ColumnHeaderCheckbox;
diff --git a/client/src/components/notification-settings/notification-settings-form.component.jsx b/client/src/components/notification-settings/notification-settings-form.component.jsx
index 82ea4ad6c..250d8ae3d 100644
--- a/client/src/components/notification-settings/notification-settings-form.component.jsx
+++ b/client/src/components/notification-settings/notification-settings-form.component.jsx
@@ -12,12 +12,13 @@ import {
   UPDATE_NOTIFICATION_SETTINGS,
   UPDATE_NOTIFICATIONS_AUTOADD
 } from "../../graphql/user.queries.js";
-import { notificationScenarios, notificationScenarioDefaults } from "../../utils/jobNotificationScenarios.js";
+import { getNotificationScenarios, notificationScenarioDefaults } from "../../utils/jobNotificationScenarios.js";
 import LoadingSpinner from "../loading-spinner/loading-spinner.component.jsx";
 import PropTypes from "prop-types";
 import { useNotification } from "../../contexts/Notifications/notificationContext.jsx";
 import ColumnHeaderCheckbox from "../notification-settings/column-header-checkbox.component.jsx";
 import { useIsEmployee } from "../../utils/useIsEmployee.js";
+import { hasDocumensoApiKey } from "../../utils/esignature.js";
 
 /**
  * Notifications Settings Form
@@ -35,6 +36,7 @@ const NotificationSettingsForm = ({ currentUser, bodyshop }) => {
   const [initialAutoAdd, setInitialAutoAdd] = useState(false);
   const notification = useNotification();
   const isEmployee = useIsEmployee(bodyshop, currentUser);
+  const notificationScenarios = getNotificationScenarios({ includeEsign: hasDocumensoApiKey(bodyshop) });
 
   // Fetch notification settings and notifications_autoadd
   const { loading, error, data } = useQuery(QUERY_NOTIFICATION_SETTINGS, {
@@ -66,7 +68,7 @@ const NotificationSettingsForm = ({ currentUser, bodyshop }) => {
       setInitialAutoAdd(autoAdd);
       setIsDirty(false); // Reset dirty state when new data loads
     }
-  }, [data, form]);
+  }, [data, form, notificationScenarios]);
 
   // Handle toggle of notifications_autoadd
   const handleAutoAddToggle = async (checked) => {
@@ -137,7 +139,14 @@ const NotificationSettingsForm = ({ currentUser, bodyshop }) => {
       width: "80%"
     },
     {
-      title: <ColumnHeaderCheckbox channel="app" form={form} onHeaderChange={() => setIsDirty(true)} />,
+      title: (
+        <ColumnHeaderCheckbox
+          channel="app"
+          form={form}
+          onHeaderChange={() => setIsDirty(true)}
+          scenarioKeys={notificationScenarios}
+        />
+      ),
       dataIndex: "app",
       key: "app",
       align: "center",
@@ -148,7 +157,14 @@ const NotificationSettingsForm = ({ currentUser, bodyshop }) => {
       )
     },
     {
-      title: <ColumnHeaderCheckbox channel="email" form={form} onHeaderChange={() => setIsDirty(true)} />,
+      title: (
+        <ColumnHeaderCheckbox
+          channel="email"
+          form={form}
+          onHeaderChange={() => setIsDirty(true)}
+          scenarioKeys={notificationScenarios}
+        />
+      ),
       dataIndex: "email",
       key: "email",
       align: "center",
@@ -163,7 +179,14 @@ const NotificationSettingsForm = ({ currentUser, bodyshop }) => {
   // Currently disabled for prod
   if (!import.meta.env.PROD) {
     columns.push({
-      title: <ColumnHeaderCheckbox channel="fcm" form={form} onHeaderChange={() => setIsDirty(true)} />,
+      title: (
+        <ColumnHeaderCheckbox
+          channel="fcm"
+          form={form}
+          onHeaderChange={() => setIsDirty(true)}
+          scenarioKeys={notificationScenarios}
+        />
+      ),
       dataIndex: "fcm",
       key: "fcm",
       align: "center",
diff --git a/client/src/components/print-center-item/print-center-item.component.jsx b/client/src/components/print-center-item/print-center-item.component.jsx
index 2cfa1b60c..0f1d69f66 100644
--- a/client/src/components/print-center-item/print-center-item.component.jsx
+++ b/client/src/components/print-center-item/print-center-item.component.jsx
@@ -12,6 +12,7 @@ import { HasFeatureAccess } from "./../feature-wrapper/feature-wrapper.component
 import { useNotification } from "../../contexts/Notifications/notificationContext.jsx";
 import axios from "axios";
 import { setModalContext } from "../../redux/modals/modals.actions.js";
+import { hasDocumensoApiKey } from "../../utils/esignature.js";
 
 const mapStateToProps = createStructuredSelector({
   printCenterModal: selectPrintCenter,
@@ -41,6 +42,7 @@ export function PrintCenterItemComponent({
   const [loading, setLoading] = useState(false);
   const { context } = printCenterModal;
   const notification = useNotification();
+  const esignatureEnabled = hasDocumensoApiKey(bodyshop);
 
   const renderToNewWindow = async () => {
     setLoading(true);
@@ -96,7 +98,7 @@ export function PrintCenterItemComponent({
     <li>
       <Space wrap>
         {item.title}
-        <SignatureFilled onClick={esignatureGenerate} />
+        {esignatureEnabled && <SignatureFilled onClick={esignatureGenerate} />}
         <PrinterOutlined onClick={renderToNewWindow} />
         {!technician ? (
           <MailOutlined
diff --git a/client/src/components/print-center-jobs/print-center-jobs.component.jsx b/client/src/components/print-center-jobs/print-center-jobs.component.jsx
index 207ae40b3..5e68f56b1 100644
--- a/client/src/components/print-center-jobs/print-center-jobs.component.jsx
+++ b/client/src/components/print-center-jobs/print-center-jobs.component.jsx
@@ -15,6 +15,7 @@ import PrintCenterJobsLabels from "../print-center-jobs-labels/print-center-jobs
 import PrintCenterSpeedPrint from "../print-center-speed-print/print-center-speed-print.component";
 import { bodyshopHasDmsKey, DMS_MAP, getDmsMode } from "../../utils/dmsUtils";
 import { selectTechnician } from "../../redux/tech/tech.selectors";
+import { hasDocumensoApiKey } from "../../utils/esignature.js";
 
 const mapStateToProps = createStructuredSelector({
   printCenterModal: selectPrintCenter,
@@ -39,6 +40,7 @@ export function PrintCenterJobsComponent({ printCenterModal, bodyshop, technicia
   const hasDMSKey = bodyshopHasDmsKey(bodyshop);
   const dmsMode = getDmsMode(bodyshop, "off");
   const isReynoldsMode = dmsMode === DMS_MAP.reynolds;
+  const esignatureEnabled = hasDocumensoApiKey(bodyshop);
 
   const Templates = !hasDMSKey
     ? Object.keys(tempList)
@@ -98,7 +100,7 @@ export function PrintCenterJobsComponent({ printCenterModal, bodyshop, technicia
             extra={
               <Space wrap>
                 <PrintCenterJobsLabels jobId={jobId} />
-                <EsignatureCustomDocument jobId={jobId} />
+                {esignatureEnabled && <EsignatureCustomDocument jobId={jobId} />}
                 <Jobd3RdPartyModal jobId={jobId} job={job} />
                 <Input.Search onChange={(e) => setSearch(e.target.value)} value={search} enterButton />
               </Space>
diff --git a/client/src/graphql/bodyshop.queries.js b/client/src/graphql/bodyshop.queries.js
index 38dd5bde4..91a230053 100644
--- a/client/src/graphql/bodyshop.queries.js
+++ b/client/src/graphql/bodyshop.queries.js
@@ -53,6 +53,7 @@ export const QUERY_BODYSHOP = gql`
       phone
       federal_tax_id
       id
+      documenso_api_key
       insurance_vendor_id
       logo_img_path
       md_ro_statuses
diff --git a/client/src/pages/jobs-detail/jobs-detail.page.component.jsx b/client/src/pages/jobs-detail/jobs-detail.page.component.jsx
index fe41869a6..ea8fc9153 100644
--- a/client/src/pages/jobs-detail/jobs-detail.page.component.jsx
+++ b/client/src/pages/jobs-detail/jobs-detail.page.component.jsx
@@ -57,6 +57,7 @@ import { selectBodyshop } from "../../redux/user/user.selectors";
 import AuditTrailMapping from "../../utils/AuditTrailMappings";
 import { DateTimeFormat } from "../../utils/DateFormatter";
 import dayjs from "../../utils/day";
+import { hasDocumensoApiKey } from "../../utils/esignature.js";
 import UndefinedToNull from "../../utils/undefinedtonull";
 
 const mapStateToProps = createStructuredSelector({
@@ -105,6 +106,7 @@ export function JobsDetailPage({
   });
   const notification = useNotification();
   const { scenarioNotificationsOn } = useSocket();
+  const esignatureEnabled = hasDocumensoApiKey(bodyshop);
 
   useEffect(() => {
     //form.setFieldsValue(transormJobToForm(job));
@@ -286,7 +288,7 @@ export function JobsDetailPage({
       >
         {t("general.labels.refresh")}
       </Button>
-      <EsignatureCustomDocument jobId={job.id} />
+      {esignatureEnabled && <EsignatureCustomDocument jobId={job.id} />}
       <JobsChangeStatus job={job} />
       <JobSyncButton job={job} />
       <Button
diff --git a/client/src/pages/manage/manage.page.component.jsx b/client/src/pages/manage/manage.page.component.jsx
index 2289b2366..34609acc8 100644
--- a/client/src/pages/manage/manage.page.component.jsx
+++ b/client/src/pages/manage/manage.page.component.jsx
@@ -31,6 +31,7 @@ import useAlertsNotifications from "../../hooks/useAlertsNotifications.jsx";
 import { selectDarkMode } from "../../redux/application/application.selectors.js";
 import { lazyDev } from "../../utils/lazyWithPreload.jsx";
 import EsignatureModalContainer from "../../components/esignature-modal/esignature-modal.container.jsx";
+import { hasDocumensoApiKey } from "../../utils/esignature.js";
 
 const PrintCenterModalContainer = lazyDev(
   () => import("../../components/print-center-modal/print-center-modal.container")
@@ -128,6 +129,7 @@ const mapStateToProps = createStructuredSelector({
 
 export function Manage({ conflict, bodyshop, partsManagementOnly, isDarkMode, currentUser }) {
   const { t } = useTranslation();
+  const esignatureEnabled = hasDocumensoApiKey(bodyshop);
   const [chatVisible] = useState(false);
   const didMount = useRef(false);
 
@@ -183,7 +185,7 @@ export function Manage({ conflict, bodyshop, partsManagementOnly, isDarkMode, cu
       <TaskUpsertModalContainer />
       <BreadCrumbs />
       <BillEnterModalContainer />
-      <EsignatureModalContainer />
+      {esignatureEnabled && <EsignatureModalContainer />}
       <JobCostingModal />
       <ReportCenterModal />
       <EmailOverlayContainer />
diff --git a/client/src/utils/esignature.js b/client/src/utils/esignature.js
new file mode 100644
index 000000000..4936b3052
--- /dev/null
+++ b/client/src/utils/esignature.js
@@ -0,0 +1,7 @@
+export const hasDocumensoApiKey = (bodyshop) => {
+  if (typeof bodyshop?.documenso_api_key === "string") {
+    return bodyshop.documenso_api_key.trim().length > 0;
+  }
+
+  return Boolean(bodyshop?.documenso_api_key);
+};
diff --git a/client/src/utils/jobNotificationScenarios.js b/client/src/utils/jobNotificationScenarios.js
index a2839b84e..7efb09f6a 100644
--- a/client/src/utils/jobNotificationScenarios.js
+++ b/client/src/utils/jobNotificationScenarios.js
@@ -2,7 +2,7 @@
  * @description This file contains the scenarios for job notifications.
  * @type {string[]}
  */
-const notificationScenarios = [
+const baseNotificationScenarios = [
   "job-assigned-to-me",
   "bill-posted",
   "critical-parts-status-changed",
@@ -16,13 +16,21 @@ const notificationScenarios = [
   "job-added-to-production",
   "job-status-change",
   "payment-collected-completed",
-  "alternate-transport-changed",
+  "alternate-transport-changed"
+  // "supplement-imported", // Disabled for now
+];
+
+const esignNotificationScenarios = [
   "esign-document-opened",
   "esign-document-completed",
   "esign-document-upload-failed"
-  // "supplement-imported", // Disabled for now
 ];
 
+const notificationScenarios = [...baseNotificationScenarios, ...esignNotificationScenarios];
+
+const getNotificationScenarios = ({ includeEsign = true } = {}) =>
+  includeEsign ? notificationScenarios : baseNotificationScenarios;
+
 /**
  * Default channel preferences for e-sign document notifications. By default, all e-sign related notifications will be
  * sent via the app, but not via email or FCM. These defaults can be overridden by user preferences.
@@ -34,4 +42,4 @@ const notificationScenarioDefaults = {
   "esign-document-upload-failed": { app: true, email: false, fcm: false }
 };
 
-export { notificationScenarios, notificationScenarioDefaults };
+export { esignNotificationScenarios, getNotificationScenarios, notificationScenarios, notificationScenarioDefaults };
diff --git a/server/esign/esign-new.js b/server/esign/esign-new.js
index 9e48c0c93..66dd661be 100644
--- a/server/esign/esign-new.js
+++ b/server/esign/esign-new.js
@@ -36,6 +36,41 @@ function getDefaultEsignData({ esigData, bodyshop, fileName }) {
     };
 }
 
+function createClientError(message, statusCode = 400) {
+    const error = new Error(message);
+    error.statusCode = statusCode;
+    return error;
+}
+
+function isValidEmail(email) {
+    return /^[^\s@]+@[^\s@]+\.[^\s@]+$/.test(email);
+}
+
+function getJobOwnerName(jobData, email) {
+    const ownerName = [jobData?.ownr_fn, jobData?.ownr_ln].filter(Boolean).join(" ").trim();
+    return ownerName || jobData?.ownr_co_nm || email;
+}
+
+function getJobOwnerRecipients(jobData) {
+    const ownerEmail = jobData?.ownr_ea?.trim();
+
+    if (!ownerEmail) {
+        throw createClientError("Job owner email is required before sending an e-signature request.");
+    }
+
+    if (!isValidEmail(ownerEmail)) {
+        throw createClientError(`Job owner email "${ownerEmail}" is not valid.`);
+    }
+
+    return [
+        {
+            email: ownerEmail,
+            name: getJobOwnerName(jobData, ownerEmail),
+            role: "SIGNER"
+        }
+    ];
+}
+
 async function getDocumensoClient({ bodyshopid, req }) {
     const client = req.userGraphQLClient;
     const { bodyshops_by_pk: { documenso_api_key } } = await client.request(QUERY_DOCUMENSO_KEY, { bodyshopid });
@@ -52,11 +87,7 @@ async function createEsignDocumentFromPdf({ req, bodyshop, pdfBuffer, esigData,
     const client = req.userGraphQLClient;
 
     const { jobs_by_pk: jobData } = await client.request(QUERY_JOB_FOR_SIGNATURE, { jobid });
-    const recipients = [{
-        email: "patrick@imexsystems.ca",
-        name: `${jobData.ownr_fn} ${jobData.ownr_ln}`,
-        role: "SIGNER",
-    }];
+    const recipients = getJobOwnerRecipients(jobData);
 
     const documenso = await getDocumensoClient({ bodyshopid: bodyshop.id, req })
 
@@ -267,7 +298,7 @@ async function newEsignDocument(req, res) {
             message: error.message, stack: error.stack,
             body: _.omit(req.body, ["bodyshop"]) // bodyshop can be large, so we omit it from the logs
         });
-        res.status(500).json({ error: "An error occurred while creating the e-sign document.", message: error.message });
+        res.status(error.statusCode || 500).json({ error: "An error occurred while creating the e-sign document.", message: error.message });
     }
 }
 
@@ -302,7 +333,7 @@ async function newCustomEsignDocument(req, res) {
             message: error.message, stack: error.stack,
             body: _.omit(req.body, ["bodyshop"]) // bodyshop can be large, so we omit it from the logs
         });
-        res.status(500).json({ error: "An error occurred while creating the custom e-sign document.", message: error.message });
+        res.status(error.statusCode || 500).json({ error: "An error occurred while creating the custom e-sign document.", message: error.message });
     }
 }
 
diff --git a/server/esign/webhook.js b/server/esign/webhook.js
index 890d8c55f..a99f2d036 100644
--- a/server/esign/webhook.js
+++ b/server/esign/webhook.js
@@ -219,8 +219,13 @@ async function handleDocumentCompleted(payload) {
         }
       };
       const formData = new FormData();
+      const fileName = document.filename?.toLowerCase().endsWith(".pdf")
+        ? document.filename
+        : `${document.filename || `esignature-document-${payload.id}`}.pdf`;
+      const pdfBlob = new Blob([buffer], { type: "application/pdf" });
+
       formData.append("jobid", jobid);
-      formData.append("file", buffer); //TODO: Validate this is the correct type.
+      formData.append("file", pdfBlob, fileName);
 
       try {
         const imexMediaServerResponse = await axios.post(
@@ -232,12 +237,9 @@ async function handleDocumentCompleted(payload) {
         if (imexMediaServerResponse.status === 200) {
           //Succesful upload - we don't really need to do anything here.
         } else {
-          logger.log(`esig-webhook-lms-upload-error`, "ERROR", "redis", "api", {
-            message: imexMediaServerResponse.statusText,
-            jobid,
-            documentId: payload.id
-          });
-          notifyUploadFailure();
+          throw new Error(
+            `Local media server upload failed with status ${imexMediaServerResponse.status}: ${imexMediaServerResponse.statusText}`
+          );
         }
       } catch (error) {
         logger.log(`esig-webhook-lms-upload-error`, "ERROR", "redis", "api", {
@@ -247,6 +249,7 @@ async function handleDocumentCompleted(payload) {
           documentId: payload.id
         });
         notifyUploadFailure();
+        throw error;
       }
     } else {
       try {
@@ -274,13 +277,9 @@ async function handleDocumentCompleted(payload) {
             }
           });
         } else {
-          logger.log(`esig-webhook-s3-upload-error`, "ERROR", "redis", "api", {
-            message: uploadResult.message,
-            stack: uploadResult.stack,
-            jobid: jobid,
-            documentId: payload.id
-          });
-          notifyUploadFailure();
+          const uploadError = new Error(uploadResult.message || "S3 upload failed");
+          uploadError.stack = uploadResult.stack || uploadError.stack;
+          throw uploadError;
         }
       } catch (error) {
         logger.log(`esig-webhook-s3-upload-error`, "ERROR", "redis", "api", {
@@ -290,6 +289,7 @@ async function handleDocumentCompleted(payload) {
           documentId: payload.id
         });
         notifyUploadFailure();
+        throw error;
       }
     }
 
@@ -328,6 +328,7 @@ async function handleDocumentCompleted(payload) {
       stack: error.stack,
       payload
     });
+    throw error;
   }
 }