Insightly

Insightly's documentation describes sending from Outlook with its sidebar, not Insightly sending through your Microsoft 365 mailbox. Choose how your CRM or app sends its mail explains the two ways to send and why.

At a glance

• Can be signed: email you write in Outlook, including with Insightly's sidebar, as any Outlook mail. Insightly says: "The email you send appears as a sent item in both Outlook and in Insightly CRM." and "You can install the Sidebar from the Microsoft Office Store."
• Cannot be signed: email Insightly sends itself. The page read does not say that Insightly sends mail through your mailbox, or how it sends.
• Status: from Insightly's documentation as read on 23 October 2026, not tested by Footer365. The article is a blog post dated 19 April 2024, so it may be out of date.

What you can do

1. Write email in Outlook with the sidebar. Footer365 signs it like any other Outlook mail, with mail flow set up or the Outlook add-in deployed. Which messages get a signature
2. Make sure each person has a Footer365 signature rule.
3. Check one message, as described in Mail from your CRM and other apps.

What is not signed

Email sent from within Insightly's own pages, because the page read does not describe how it is sent. Footer365 never sees mail sent from Insightly's own servers. A connector into Exchange Online is not an option: Microsoft says SMTP relay cannot be used for a service hosted by someone else. Last resort: a connector to Exchange Online

If it does not work

1. A message written in Outlook is unsigned. The signature was not added
2. A message from Insightly has no X-Footer365-Relay-Id. It did not pass through Microsoft 365 with Footer365. Mail from our CRM is not signed

Sources

Read on 23 October 2026:

• Insightly: Using Microsoft products and apps with Insightly CRM, 19 April 2024.