diff --git a/packages/features/ee/workflows/api/scheduleEmailReminders.ts b/packages/features/ee/workflows/api/scheduleEmailReminders.ts
index c683667325..a51c17a266 100644
--- a/packages/features/ee/workflows/api/scheduleEmailReminders.ts
+++ b/packages/features/ee/workflows/api/scheduleEmailReminders.ts
@@ -352,6 +352,13 @@ async function handler(req: NextRequest) {
             title: booking.title || booking.eventType?.title || "",
           };
 
+          const customReplyTo = reminder.booking?.eventType?.customReplyToEmail;
+              const fallbackReplyTo =
+                reminder.booking?.userPrimaryEmail ?? reminder.booking?.user?.email;
+              const replyTo = reminder.booking?.eventType?.hideOrganizerEmail
+                ? customReplyTo
+                : customReplyTo ?? fallbackReplyTo;
+
           const mailData = {
             subject: emailContent.emailSubject,
             to: Array.isArray(sendTo) ? sendTo : [sendTo],
@@ -367,13 +374,8 @@ async function handler(req: NextRequest) {
                 ]
               : undefined,
             sender: reminder.workflowStep.sender,
-            ...(!reminder.booking?.eventType?.hideOrganizerEmail && {
-              replyTo:
-                reminder.booking?.eventType?.customReplyToEmail ??
-                reminder.booking?.userPrimaryEmail ??
-                reminder.booking.user?.email,
-            }),
-          };
+          ...(replyTo ? { replyTo } : {}),
+        };
 
           if (isSendgridEnabled) {
             sendEmailPromises.push(
@@ -448,18 +450,19 @@ async function handler(req: NextRequest) {
         });
         if (emailContent.emailSubject.length > 0 && !emailBodyEmpty && sendTo) {
           const batchId = isSendgridEnabled ? await getBatchId() : undefined;
+          const customReplyTo = reminder.booking?.eventType?.customReplyToEmail;
+          const fallbackReplyTo =
+            reminder.booking?.userPrimaryEmail || reminder.booking?.user?.email;
+          const replyTo = reminder.booking?.eventType?.hideOrganizerEmail
+            ? customReplyTo
+            : customReplyTo || fallbackReplyTo;
 
           const mailData = {
             subject: emailContent.emailSubject,
             to: [sendTo],
             html: emailContent.emailBody,
             sender: reminder.workflowStep?.sender,
-            ...(!reminder.booking?.eventType?.hideOrganizerEmail && {
-              replyTo:
-                reminder.booking?.eventType?.customReplyToEmail ||
-                reminder.booking?.userPrimaryEmail ||
-                reminder.booking.user?.email,
-            }),
+            ...(replyTo ? { replyTo } : {}),
           };
           if (isSendgridEnabled) {
             sendEmailPromises.push(
diff --git a/packages/features/ee/workflows/lib/service/EmailWorkflowService.ts b/packages/features/ee/workflows/lib/service/EmailWorkflowService.ts
index c55b3dd8bc..22c6483b05 100644
--- a/packages/features/ee/workflows/lib/service/EmailWorkflowService.ts
+++ b/packages/features/ee/workflows/lib/service/EmailWorkflowService.ts
@@ -571,12 +571,14 @@ export class EmailWorkflowService {
     const customReplyToEmail =
       evt?.eventType?.customReplyToEmail || (evt as CalendarEvent).customReplyToEmail;
 
+    const replyTo = evt.hideOrganizerEmail
+      ? customReplyToEmail
+      : customReplyToEmail || evt.organizer.email;
+
     return {
       subject: emailContent.emailSubject,
       html: emailContent.emailBody,
-      ...(!evt.hideOrganizerEmail && {
-        replyTo: customReplyToEmail || evt.organizer.email,
-      }),
+      ...(replyTo && { replyTo }),
       attachments,
       sender,
     };
diff --git a/packages/lib/getReplyToHeader.ts b/packages/lib/getReplyToHeader.ts
index 22b3425e3e..36254dfe54 100644
--- a/packages/lib/getReplyToHeader.ts
+++ b/packages/lib/getReplyToHeader.ts
@@ -7,9 +7,7 @@ export function getReplyToHeader(
   additionalEmails?: string | string[],
   excludeOrganizerEmail?: boolean
 ) {
-  if (calEvent.hideOrganizerEmail) return {};
-
-  const replyToEmail = getReplyToEmail(calEvent, excludeOrganizerEmail);
+  const replyToEmail = getReplyToEmail(calEvent, excludeOrganizerEmail ?? calEvent.hideOrganizerEmail);
   const emailArray: string[] = [];
 
   if (additionalEmails) {