diff --git a/packages/core/src/libraries/organization-invitation.ts b/packages/core/src/libraries/organization-invitation.ts
index ad27fb2dfa05..17859be08bd1 100644
--- a/packages/core/src/libraries/organization-invitation.ts
+++ b/packages/core/src/libraries/organization-invitation.ts
@@ -66,6 +66,11 @@ export class OrganizationInvitationLibrary {
 
     return this.queries.pool.transaction(async (connection) => {
       const organizationQueries = new OrganizationQueries(connection);
+      // Check if any pending invitation has expired, if yes, update the invitation status to "Expired" first
+      // Note: Even if the status may appear to be "Expired", the actual data in DB may still be "Pending".
+      // Check `findEntities` in `OrganizationQueries` for more details.
+      await organizationQueries.invitations.updateExpiredEntities({ invitee, organizationId });
+      // Insert the new invitation
       const invitation = await organizationQueries.invitations.insert({
         id: generateStandardId(),
         inviterId,
diff --git a/packages/core/src/queries/organization/index.ts b/packages/core/src/queries/organization/index.ts
index 9a44a065a79b..b3e7303d10d9 100644
--- a/packages/core/src/queries/organization/index.ts
+++ b/packages/core/src/queries/organization/index.ts
@@ -116,6 +116,33 @@ class OrganizationInvitationsQueries extends SchemaQueries<
     return this.pool.any(this.#findEntity({ ...options, invitationId: undefined }));
   }
 
+  async updateExpiredEntities({
+    invitationId,
+    organizationId,
+    inviterId,
+    invitee,
+  }: OrganizationInvitationSearchOptions): Promise<void> {
+    const { table, fields } = convertToIdentifiers(OrganizationInvitations);
+    await this.pool.query(sql`
+      update ${table}
+      set ${fields.status} = ${OrganizationInvitationStatus.Expired}
+      where ${fields.status} = ${OrganizationInvitationStatus.Pending}
+      and ${fields.expiresAt} < now()
+      ${conditionalSql(invitationId, (id) => {
+        return sql`and ${fields.id} = ${id}`;
+      })}
+      ${conditionalSql(organizationId, (id) => {
+        return sql`and ${fields.organizationId} = ${id}`;
+      })}
+      ${conditionalSql(inviterId, (id) => {
+        return sql`and ${fields.inviterId} = ${id}`;
+      })}
+      ${conditionalSql(invitee, (email) => {
+        return sql`and ${fields.invitee} = ${email}`;
+      })}
+    `);
+  }
+
   #findEntity({
     invitationId,
     organizationId,