MailTail FAQ

Question 1

Is MailTail free?

Accepted Answer

Yes, MailTail has a free plan for up to 5 users with 1 signature, including the Outlook add-in and Microsoft 365 integration. Free signatures carry a small 'by MailTail' line. Upgrade any time for more users and signatures, and to remove the branding.

Question 2

How does the 14-day free trial work?

Accepted Answer

Sign up and connect your Microsoft 365 account - signatures are applied to your users instantly. You get full access to all features during the 14-day trial. At the end of the trial, billing begins automatically or you can cancel anytime.

Question 3

How is billing calculated?

Accepted Answer

Monthly plans are billed at the end of each billing cycle based on your peak user count during that period. Annual plans are paid upfront for all seats at a 15% discount.

Question 4

What Microsoft 365 plans are supported?

Accepted Answer

MailTail works with all Microsoft 365 Business and Enterprise plans that include Outlook. This includes Microsoft 365 Business Basic, Standard, Premium, and all Enterprise E1, E3, E5 plans.

Question 5

How do signatures get applied to emails?

Accepted Answer

MailTail uses an Outlook add-in that runs automatically when users compose new emails. The add-in fetches the user's assigned signature and applies it instantly.

Question 6

What data do you need from Entra ID?

Accepted Answer

We request read access to basic user profile information (name, email, job title, department, phone numbers) to populate signature placeholders. We don't access emails, files, or any other sensitive data.

Question 7

Can different departments have different signatures?

Accepted Answer

Yes! You can create multiple signature templates and assign them to different security groups. Marketing can have one design, Sales another, and Support a third.

Question 8

What happens if I cancel?

Accepted Answer

If you cancel, your signatures will stop being applied to new emails. Existing emails keep their signatures. There's no data lock-in - you can export your signature templates at any time.

Question 9

Why don't you support server-side signature injection?

Accepted Answer

Server-side injection requires Microsoft transport rules and exchange connectors, which adds significant complexity and potential points of failure. Our add-in approach is simpler to deploy, easier to troubleshoot, and gives users a live preview of their signature as they compose.

Question 10

Does MailTail work on Outlook mobile?

Accepted Answer

Yes! As of v1.1.0, MailTail works on Outlook for iOS and Android. Mobile support is deployed automatically with the add-in. Your default signature applies on mobile just like desktop, and individual users can choose whether to use signatures on mobile through their preferences.

Question 11

Do you support shared mailboxes?

Accepted Answer

Shared mailboxes work when accessed through your main user account in Outlook (e.g. adding them to your sidebar and using Send As). The add-in applies signatures because you are still in your licensed user's context. Full shared mailbox support for other access methods is on our roadmap.

Question 12

Is my data secure?

Accepted Answer

Yes. We use industry-standard encryption for data in transit and at rest. We're hosted on secure cloud infrastructure and follow Microsoft's best practices for partner applications. We never access or store your email content.

Help & Documentation

Getting Started

Installing the MailTail Outlook add-in

Requirements and supported environments

Automatic signatures in classic Outlook for Windows

Troubleshooting

The add-in isn't updating, or the version looks wrong

My signature isn't appearing on new emails

Sending is blocked, slow, or shows an add-in error

My name, title, phone or company is blank in the signature

The add-in hasn't appeared after deploying it