Freshdesk

Freshdesk can send a support address's mail through a Microsoft 365 mailbox, and Footer365 signs mail that passes through your Microsoft 365. Choose how your CRM or app sends its mail explains the two ways to send, and this guide follows the first.

At a glance

• Can be signed: ticket email sent from a support address that you added with Microsoft Office 365 and set up for outgoing email.
• Cannot be signed: an address on your own domain that has no outgoing server set up. Freshdesk says: "Freshworks will automatically assign its own mail server for outgoing emails."
• How it connects: a Microsoft sign-in. The article says to select Microsoft Office 365, "log in with your credentials, and authorize (read/write/delete) access to Freshdesk", and its server table lists smtp.office365.com on port 587 for sending.
• Status: from Freshdesk's documentation as read on 23 October 2026, not tested by Footer365.

Before you start

• Footer365 mail flow is set up. With the Outlook add-in only, no mail Freshdesk sends is signed. Using the Outlook add-in only
• The mailbox you connect has a Footer365 signature rule that covers it.
• You sign in to Freshdesk as an administrator.

Step 1: Approve the app in Microsoft 365

Freshdesk's article does not say whether an administrator has to approve it, or which Microsoft permissions it asks for beyond read, write and delete access to the mailbox. If Microsoft shows "Need admin approval", approve it by one of the three ways in Approve an app's access in Microsoft 365.

Step 2: Choose the mailbox

• A user mailbox is what the article describes. The mail is signed with the signature your rules give that mailbox, so a support address needs a rule of its own.
• A shared mailbox: Freshdesk's article does not mention shared mailboxes. Do not assume it works.

Step 3: Connect it in Freshdesk

Following Freshdesk's steps, as an administrator:

1. Go to Admin > Channels > Support Email > New Support Email.
2. Choose the setup you want: incoming only, outgoing only, or both. Replies can leave through Microsoft 365 only if the setup includes outgoing email.
3. Select Microsoft Office 365, sign in with the mailbox's credentials, and authorise the access Freshdesk asks for.

Freshdesk's own steps: Set up emails on Gmail, Microsoft Office, and other customer servers.

Step 4: Check one message

1. Reply to a test ticket from an address outside your organisation that you can read.
2. Open the headers of the copy you receive.
3. Return-Path should be the support mailbox's address, and X-Footer365-Relay-Id should be there.
4. Look in the mailbox's Sent Items. Freshdesk's article does not say whether the reply is saved there.

If the headers show Freshworks' servers and no X-Footer365-Relay-Id, Freshdesk sent the reply itself: check the support address has an outgoing server. What other results mean: Mail from our CRM is not signed.

Where the signature goes

Freshdesk's article does not describe a signature setting for a connected support email. If you see two signatures, remove Freshdesk's. To place Footer365's signature in a template, use a marker, and check one message, because the article does not say what Freshdesk does with text in double braces. Place the signature with a marker

What is not signed

Freshdesk says that for an address on a non-public domain, such as [email protected], "Freshworks will automatically assign its own mail server for outgoing emails", and that an address on a public domain defaults to the incoming provider's server and can be changed later. A support address on your own Microsoft 365 domain is a non-public domain. The article does not say whether connecting it with Microsoft Office 365, as in step 3, replaces that default, so check one message to see whether its replies leave through Microsoft 365. If they leave from Freshworks' server they are not signed.

What stops working

• Token renewal. Freshdesk says: "You may have to reauthenticate your tokens every 90 days." When the token lapses, Freshdesk can no longer send through the mailbox, so connect it again.
• Basic authentication. The article does not say whether Freshdesk's SMTP sending uses OAuth or a stored password. Microsoft has announced that Basic authentication for SMTP is turned off by default for existing organisations at the end of December 2026. Turn on SMTP sign-in for one mailbox

Limits

Freshdesk's article states no sending limit. Microsoft's limits for a mailbox apply: 10,000 recipients a day and 30 messages a minute. Microsoft: Exchange Online limits

Last resort: a connector to Exchange Online

Freshdesk's article describes no connector from Freshdesk into Exchange Online, and Freshdesk runs on Freshworks' servers. Microsoft says SMTP relay cannot be used for a service hosted by someone else, and asks such a service for a certificate of your own. So there is no connector route for Freshdesk mail. Last resort: a connector to Exchange Online

If it does not work

1. Replies stop after about 90 days. Reauthenticate the mailbox in Freshdesk.
2. Microsoft says "Need admin approval". Approve an app's access in Microsoft 365
3. The message has no X-Footer365-Relay-Id. It did not pass through Microsoft 365. Check the outgoing server, as in step 3.
4. It passed through Footer365 but is unsigned. The wrong signature is used for a shared mailbox or delegate
5. Still not clear. Mail from our CRM is not signed

Sources

Read on 23 October 2026:

• Freshdesk: Set up emails on Gmail, Microsoft Office, and other customer servers, modified 21 January 2026.