Outlook 365 for Mac OS mis-locates signatures

TidBITS Talk
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For over 2.5 years, when replying to emails, MS Outlook 365 for MacOS puts the pre-designated signatures below the heading/email address, etc. of the original email rather than at the bottom of the reply email. I have spent many hours with MS help desks, sending them examples, etc. Over a year ago I was told that their engineers were well aware of the problem and I should monitor Outlook updates to see when it is fixed. I have done that to no avail. Ugh. I am tired of manually moving the signatures from the older email into the new replies.

Any ideas out there on a fix or how to get into the Microsoft help world at a high enough level to pay attention to the problem?

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Guy, I did not recall having this problem the last time I worked in a corporate environment that used MS Exchange in the cloud for email service, plus Outlook 365 on the Macs and PCs (nearly three years ago). My Macs always put my signature up top when I was replying and forwarding messages. So I asked CoPilot about this. Here is what it said:

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You’re remembering something real — but the explanation is a bit counter‑intuitive. Outlook for Mac used to behave differently in certain corporate Exchange environments, but not because Exchange controlled signature placement. The difference came from which Outlook client you were using and how signatures were synced, not from the server.

Here’s the full picture, clearly laid out.

:white_check_mark: Why your signature used to appear at the top in your old corporate job

There are two generations of Outlook for Mac:

1. “Legacy Outlook for Mac” (pre‑2021)

  • This version did place signatures directly under your reply text.

  • It behaved much more like Outlook for Windows.

  • Many corporate environments stayed on this version longer because:

    • It supported on‑prem Exchange features

    • It supported advanced corporate mailbox features the “New Outlook” didn’t yet have

2. “New Outlook for Mac” (2021–present)

  • This is the version most people now use.

  • It always places signatures at the very bottom of the entire thread when replying or forwarding.

  • Microsoft removed the option to control signature placement.

  • This behavior is the same for:

    • Exchange Online

    • Exchange on‑prem

    • Microsoft 365

    • IMAP

    • Gmail

So the difference you experienced was client version, not server type.

:puzzle_piece: What about Outlook Web (OWA)?

Outlook Web App does place signatures directly under your reply text.

But — and this is key —
OWA settings do NOT sync signature placement behavior to Outlook for Mac.

The only thing that syncs is the signature content (in the New Outlook), not the placement logic.

So even if OWA inserts signatures correctly, Outlook for Mac will still put them at the bottom.

:magnifying_glass_tilted_left: Why corporate environments sometimes “felt” different

Many companies:

  • Disabled the New Outlook toggle for employees

  • Or employees stayed on Legacy Outlook for Mac because it supported features the New Outlook didn’t

That older client had the behavior you remember.

:hammer_and_wrench: Can this be fixed today?

Unfortunately, no setting exists in the New Outlook for Mac to change signature placement.

Your options remain:

  • Use Legacy Outlook (if still available)
    (Microsoft is phasing it out, but some builds still allow switching back)

  • Disable automatic signatures for replies and insert manually

  • Use a text expansion shortcut to insert your signature exactly where you want

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So Guy, if you’re in a corporate/Exchange/M365 environment, you might be able to use web mail to avoid this signature placement issue, or else fall back to the legacy version of Outlook for Mac (what I used to use on the job), which should also work in a non-corporate non-Exchange/M365 environment, provided you don’t mind giving up any features only available in the New Outlook. Other than that, you could follow some of the work-arounds CoPilot suggested, such as inserting the signature manually or using a text expansion shortcut.

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I’m still on the Legacy version of Outlook through a Microsoft 365 Business subscription, but support ends in October for most people (see table at the bottom of the link below).

It’s a pity. The program certainly has its quirks, but once you get used to them, Legacy Outlook is pretty capable.

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ProTourist:

Thank you very very much for your most helpful, if disappointing, reply. I’m a stand alone small business operator who switched from Legacy Outlook to New Outlook 365 a number of years ago and began trying to get help from the MS help facility. Your and CoPilot’s post have made me realize I simply need to continue to select and move the mis-placed signature block up into the reply/forward messages and give up on ever having a solution! Fortunately I’m a low volume business and it is almost automatic now.

Thanks again.

Guy Towle
guytowle@comcast.net

Someone replied to your post.

| ProTourist
May 19 |

  • | - |

Guy, I did not recall having this problem the last time I worked in a corporate environment that used MS Exchange in the cloud for email service, plus Outlook 365 on the Macs and PCs (nearly three years ago). My Macs always put my signature up top when I was replying and forwarding messages. So I asked CoPilot about this. Here is what it said:

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I work in on a corporate MS 365 account with the latest Outlook for Mac on machine. The signature always goes to the end of my reply, not the entire thread. I have never had it go to the bottom of the thread that I can recall. I have been on the latest iteration of MS 365 for at least the pandemic. Am I lucky?

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Thanks very much for linking that support article, josehill. Good information, if not good news.

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Glad to be of help, Guy. I find Gemini and CoPilot to be quite useful for troubleshooting, and also find discussion easier than searching for and reading several support articles. Gemini especially is good at explaining things in the way the person needs, to understand best. The biggest issues I have with these AI agents as troubleshooting helpers is that 1) if it goes on for a while, they start repeating previous advice that did not work, and 2) they don’t have a lot of common sense – meaning that they might propose an alternative that doesn’t have the issue you’re facing, without telling you (or perhaps even realizing) that it has a different, even bigger issue.

Anyway, remember that you can turn off the auto-placement of the signature in Outlook’s preferences, and then just click the Signature button in the ribbon to place the signature where you want it. That way you could avoid the scrolling and the cut/paste. Cheers.

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Earl, I would guess that you’re using the Legacy version of Outlook for Mac, perhaps without realizing it. Your company’s email admin may have disabled New Outlook on the server side. But if that’s the case, based on the Microsoft support article that josehill linked above, the Legacy version will be going away in October. :unamused_face:

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That is kind of funny since I am the admin and I never disabled New Outlook. The version on my Mac is Version 16.109 (26051019).

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Earl, I would still guess that you are running Legacy Outlook even if the admin (yourself) has not disabled the New Outlook. At one point you may have switched the interface on your Mac from the New to the Legacy, via either a toggle switch or a menu option. The easiest way to tell is probably just by the look and feel of the user interface, if you are running Legacy or New. This video gives some examples:

https://www.youtube.com/watch?v=snU0cMfnV6s

By the way, “Legacy” does not mean an older version of the application, but an older version of the user interface and of the Outlook database format. The application version number should be the same regardless of which interface is used. [If someone has used both New and Legacy, there will be two databases present in the home library folder. If for example a person switches periodically between the two formats, the one that hasn’t been used for a while will be out of date and will need to sync with the mail server in order to bring in the new data created/received since the last time it was used.]

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I am sorry to disagree. I am on the New Outlook. I have been since it came out. As the Admin, I needed to understand it to support others. I understand the differences. To confirm, I went into the Entra sign-in events and saw only non-legacy connections. I also went to the Admin usage and saw only non-legacy connections. No one in my org is using legacy connections. I am highly confident I am on the “New Outlook”. I can see two places that offer to switch me to “Legacy Outlook.” And, my automatic signature always shows up at the end of my reply, not at the end of the thread.

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Okay Earl, I believe you. But I have no explanation as to why you have no signature placement issues for reply and forward emails – nor how to find out. Maybe some things work differently in your instance of M365, or for you specifically since you are the email admin. It might be worth checking if any other non-admin Mac users in your org have different signature-placement behavior in their New Outlook. [I’m assuming that your org uses MS Exchange for email, either on-premises or in the cloud.]

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Earl, here is one more checklist from CoPilot, on the few potential ways you might receive Legacy-style signature positioning while working in New Outlook. I’m sure that #5 is not the case, but I’m including the whole list.

Signature Placement Diagnostic Checklist

Purpose: Determine why signatures appear at the top of replies/forwards in the New Outlook for Mac, even though this behavior is normally impossible with Outlook’s built‑in signature engine.

1. Verify the Actual Composer Being Used

Even in the New Outlook UI, Outlook may silently fall back to the Legacy composition engine.

  • Reply to any email → inspect the formatting toolbar

  • If it differs from the standard New Outlook toolbar, Legacy composer is active

Follow‑up: Check if New Outlook is using Legacy composer

2. Check for Server‑Side Signature Tools

These tools can insert signatures during composition and place them at the top:

  • Exclaimer

  • CodeTwo

  • Crossware

  • Tines

  • Custom transport‑rule signature systems

Test: Disable Outlook’s built‑in signature → reply → see if a signature still appears.

Follow‑up: Check if organization uses server‑side signature tool

3. Check for Outlook Add‑ins That Inject Signatures

Some add‑ins override Outlook’s signature placement.

  • Outlook → Settings → Add‑ins → disable all → restart → test reply

Follow‑up: Check for signature‑related Outlook add‑ins

4. Confirm the Update Channel

Experimental builds may behave differently:

  • Current Channel (Preview)

  • Insider Slow

  • Insider Fast

Follow‑up: Check Outlook update channel on Mac

5. Ensure the User Is Not Composing in OWA

OWA always places signatures at the top and looks similar to New Outlook.

Follow‑up: Verify if user is composing in OWA

6. Check for Text Expansion or Snippet Tools

These insert signatures exactly where the cursor is:

  • macOS text replacements

  • TextExpander

  • Keyboard Maestro

  • Quick Parts

  • Snippets in third‑party tools

Follow‑up: Check for text expander signature insertion

7. Confirm the Signature Is Outlook’s Built‑In Signature

Users sometimes use templates or snippets without realizing it.

Test:
Outlook → Settings → Signatures → delete all → reply → see what happens.

Follow‑up: Verify signature is Outlook built‑in signature

8. Identify Which Mailbox the Reply Is Coming From

Some mailbox types force Legacy composition behavior:

  • On‑prem Exchange

  • Hybrid Exchange

  • Shared mailboxes

  • Delegated mailboxes

  • Public folder mailboxes

Follow‑up: Check which mailbox is used for reply

9. Check for the Legacy Outlook Toggle

Some builds still include:

  • “Revert to Legacy Outlook”

  • “New Outlook” toggle

Even if the UI says “New Outlook,” the toggle may not be active.

Follow‑up: Check for Legacy Outlook toggle on Mac

Conclusion

If signatures appear at the top in the New Outlook, one of the nine conditions above is definitely true. The New Outlook’s built‑in signature engine never places signatures at the top on its own.

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If we could determine why you have signature at top for replies and forwards, such as through an Outlook add-in or server-side signature tool, it might actually help Guy to find a solution to his problem.

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Hello again:

And thanks gain for you help and helpful posts.

Wanted to pass on what happened when I took your suggestion and turned off the auto-placement feature and then just clicked on the “Signature” button. It still put it below the header of the older email I am replying to! This was regardless of me moving the cursor around for the type in starting point. I’m still experimenting with the three email accounts that Outlook acts as email client for but my initial foray didn’t solve the issue.

Fun stuff!

Guy Towle
guytowle@comcast.net

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Guy, I think something funky is going on. I would suggest that you have a good discussion with CoPilot about this, and see what it can come up with. https://copilot.microsoft.com/ No need to sign in.

But before you do that, it might be useful to test from another account on your Mac, creating a new local user if needed. Log out of your personal account, then log in to the Mac using the other local account. Then set up Outlook within that other Mac user for just one email account. Create a signature, without auto-placement, then test replying or forwarding a message and using the Signature button on the ribbon to place the signature where you want it, where-ever the insertion point is placed.

If the signature is still appended to the bottom of the thread, then the issue would appear to be systemic. But if the signature is inserted right where you want it, then the issue would be within your user account – there could be an Outlook add-in or something else installed locally within your Mac account interfering with the manual placement of the signature in Outlook.

The issue could possibly be related to the fact that there are multiple email accounts set up in your Outlook, and/or the mailbox types they are.

CoPilot should be able to help you to narrow this down.

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I don’t use the signature feature in my email clients, because I switch between two client apps (Apple Mail and MailMaven) and a couple of webmail clients, and I have a few different signatures for different roles. Instead, I use my snippet expander (Typinator) to enter my signature on emails. If your signature is simple, the built-in text replacement feature in MacOS might suffice.

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