Hi @Hailey Warnet ,
Are you using the web version of outlook? There's an active advisory going on at the moment about signature issues.
EX252201
Title: Users on Outlook on the web are noticing that signatures in email messages aren't showing up
User Impact: Users on Outlook on the web are noticing that signatures in email messages aren't showing up as expected.
More info: Users with email signatures already attached notice that the signature isn't appearing when creating new emails.
Users may also notice that options "Automatically include my signature on new messages that I compose" and "Automatically include my signature on messages I forward or reply to" are appearing as unchecked after refreshing.
Current expected resolution is set for later today. We've had users in our environment experiencing the same issue