Sending, receiving, and organizing email in Outlook on the web for business
This usually comes down to signature settings or message format.
First check Outlook → Settings / Options → Signatures and make sure a signature is selected for New messages and also for Replies and forwards — they’re separate options.
Also check the email format. If you’re replying in plain text, signatures with formatting or images may not appear. Switching the message format back to HTML often fixes it.
If it suddenly stopped working, try restarting Outlook or signing out and back in (for Outlook Web). Profile or sync glitches can sometimes reset signature behavior.
If you run into this often, proffesionals create signatures using tools like MySignature and reapply them quickly instead of rebuilding them inside Outlook each time.