Microsoft now ships two very different applications under the same name. Half the instructions online describe menus that no longer exist in the version you are running.
This guide covers both, tells you how to work out which one you have, and explains what happens to your signature when you switch.
Look at the top-right corner of the window. If there is a toggle labelled New Outlook, you are in the classic desktop application. If the toggle is switched on, or there is no File menu in the top-left, you are in new Outlook.
New Outlook is essentially Outlook on the web wrapped in a desktop shell, which is why its settings look nothing like the old ones.
The same steps work in new Outlook for Windows and in Outlook on the web.
If you are pasting a signature you built elsewhere, copy it from a rendered preview in your browser rather than copying raw HTML code.
There is a faster route: start a new email, click Signature on the Message ribbon, and choose Signatures from the dropdown.
Open Outlook → Settings → Signatures, click the plus button, and build the signature. Assign defaults per account in the same panel.
Mac Outlook has its own quirks with pasted HTML, particularly around table spacing. Always send yourself a test message before rolling a signature out to a team.
Classic Outlook stores signatures as local files on your machine, in %APPDATA%\Microsoft\Signatures, as a set of .htm, .rtf and .txt files for each signature.
New Outlook stores signatures server-side, attached to the mailbox. That means they follow you to any device you sign into — but it also means they do not roam across to classic Outlook, and they are not simply sitting in a folder you can edit.
There is no import button. The reliable method is to copy the rendered signature rather than the file.
Expect to do some cleanup. Which brings us to the next point.
New Outlook renders signatures with a web engine rather than the Word engine classic Outlook uses. Most of the time this is an improvement, but signatures built for the old renderer can shift.
The things to check after migrating:
If images disappear entirely during the move, our guide to signature images not showing covers the likely causes.
A signature made with the Mail Ink generator uses clean, table-based HTML with hosted images, which renders consistently in classic Outlook, new Outlook, Outlook on the web and Outlook for Mac. You build it once and paste the same thing wherever you need it.