Freshsales

Freshsales connects each person's Microsoft 365 mailbox with Microsoft Graph, 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: email sent through a person's connected Microsoft 365 mailbox, up to the limit below.
• Cannot be signed: email Freshworks sends with its product SMTP. Freshworks says: "Once you have exhausted this limit, it will automatically switch to product SMTP". It does not say which kinds of email the 300-a-day limit applies to.
• How it connects: "The web application uses Modern Authentication to connect your mailbox." and "by default, we have disabled SMTP and moved to Graph API so you can connect your email in a more secure and stable manner."
• Status: from Freshworks' documentation as read on 23 October 2026, not tested by Footer365. The connection article is dated 30 March 2024 and the limits article 10 December 2024, so check one message.

Before you start

• Footer365 mail flow is set up. With the Outlook add-in only, no mail Freshsales sends is signed. Using the Outlook add-in only
• Every person who sends from Freshsales has a Footer365 signature rule that covers them.
• Freshworks says to make sure the mailbox has API access enabled.

Step 1: Approve the app in Microsoft 365

Freshworks' connection article says nothing about administrator approval or consent. If Microsoft shows "Need admin approval", approve Freshsales by one of the three ways in Approve an app's access in Microsoft 365, after reading the permissions on Microsoft's screen.

Step 2: Choose the mailbox

• Each person's own mailbox is what Freshsales connects. The mail is signed with the signature your rules give that person.
• A shared mailbox: Freshworks' article does not cover it. Do not assume it works.
• Aliases: Freshworks says: "You cannot send email using aliases." Mail goes out from the connected mailbox's own address.

Step 3: Connect it in Freshsales

Following Freshworks' steps:

1. Go to Profile Settings and select Connect your email.
2. Select Microsoft Outlook. A pop-up opens for the email sync.
3. Choose a sync type. Two-way sync is the default. Freshworks says one-way sync limits incoming email.
4. You are sent to Microsoft's sign-in page. Select Connect email to grant the access Microsoft asks for.

Freshworks' own steps: How to connect my Microsoft 365 email account.

Step 4: Check one message

1. Send an email from Freshsales to an address outside your organisation that you can read.
2. Open the headers of the copy you receive.
3. Return-Path should be the sender's own address, and X-Footer365-Relay-Id should be there.
4. Look in the sender's Sent Items. Freshworks' pages do not say whether the message is saved there.

Check it again after a busy day, because of the limit below. What other results mean: Mail from our CRM is not signed.

Where the signature goes

Freshworks' pages read do not describe a signature setting for the connected mailbox. If you see two signatures, remove Freshsales's. To place Footer365's signature in a template, use a marker, and check one message, because Freshworks' pages do not say what Freshsales does with text in double braces. Place the signature with a marker

What is not signed

Mail sent by Freshworks' product SMTP. Freshworks says "you will be able to send upto 300 emails though your connected mailbox", and "Once you have exhausted this limit, it will automatically switch to product SMTP and continue sending through that." From then on the mail leaves from Freshworks' own servers and is not signed. Freshworks lists the product SMTP daily limits by plan for individual, bulk, workflow and sequence email, so those kinds of email can use it. A busy day can leave the later messages unsigned.

What stops working

• The EWS option. Freshworks says: "If your IT team has restricted API access to your mailbox then you can use Exchange Web Services (EWS)", and "EWS connection for Microsoft emails is available only from the Pro plan." Microsoft starts switching Exchange Web Services off in October 2026 and finishes in April 2027, so do not choose it. Exchange Web Services is being switched off
• SMTP. Freshworks says it has disabled SMTP by default and moved to the Graph API, so the default connection uses Microsoft Graph and not a stored SMTP password.

Limits

• Connected mailbox: about 300 emails a day, and then product SMTP, as above. Freshworks' limits for product SMTP, per active user, are: Growth 200 individual and 250 bulk; Pro 500 individual and 1,000 bulk; Enterprise 1,000 individual and 5,000 bulk. The page lists workflow and sequence limits too.
• Size and aliases: Freshworks says: "If the email body exceeds 4 MB, you cannot send the email." and "You cannot send email using aliases."
• Microsoft's limits for a mailbox: 10,000 recipients a day and 30 messages a minute. Microsoft: Exchange Online limits

Last resort: a connector to Exchange Online

Freshsales' pages describe no connector from Freshsales into Exchange Online, and Freshsales 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 Freshsales mail, and mail over the limit cannot be signed. Last resort: a connector to Exchange Online

If it does not work

1. A person cannot connect. Check the mailbox has API access enabled and is hosted in Exchange Online. If Microsoft says "Need admin approval", see step 1.
2. Only some messages are signed. The later ones may have gone by product SMTP after the 300-a-day limit.
3. The message has no X-Footer365-Relay-Id. It did not pass through Microsoft 365.
4. It passed through Footer365 but is unsigned. The signature was not added
5. Still not clear. Mail from our CRM is not signed

Sources

Read on 23 October 2026:

• Freshworks: How to connect my Microsoft 365 email account, modified 30 March 2024.
• Freshworks: What is the sales email limit for an account per day, modified 10 December 2024.