Open your HTML email signature file in your Safari browser.
Press Cmd + A to select the entire email signature, then press Cmd + C to copy it.
IMPORTANT: Do not use your mouse to select the area, only use Cmd + A as you may miss out on grabbing some of the code.
Open Outlook in your Safari web browser and click the Settings icon at the top right of your screen. Select Account, then Signatures from the left menus.
Click the New Signature button and enter a name for your email signature. Click inside the text box below, then press Ctrl + V (Cmd + V for Mac) to paste your copied email signature.
Under Select Default Signatures, select your signature name for New Messages and Replies/Forwards. Hit Save.
Close out of your settings and compose a new email. Your email signature will now automatically insert.
Download and install our macOS Signature Installer App.
Run the app once, then you can Quit using the icon at the bottom left of the app.
Open Safari and from your menu bar select Safari, then Preferences. Go to the Extensions tab and enable Email Signature Rescue.
Once enabled, an ESR icon will appear on your Safari toolbar to the left of your URL address bar. Click the extension icon to expand the extension, then complete the steps to install your email signature.
Select Outlook from the first drop down box. Enter the email address that you'd like the email signature to apply to. And finally, insert your signature key and click Install.
Your email signature will now automatically insert when composing an email within Outlook for Web in Safari.