Outlook 2021 sent e-mails show attachment icon without any attachments.

I recently switched over from POP3 to IMAP, since I'm now on a 2nd desktop computer (running Windows 11) in addition to my original laptop (running Windows 10).

In doing the switching over and setting up of IMAP mail accounts, I had a bit of a learning curve in how to set things up, but I dealt with and figures these out via some self-help and some additional reading (including a post on this forum).

One thing I cannot figure out is after adding my e-mail signatures to both machines (an HTML signature with image + hyperlink on image), every time I send an e-mail even without attachments, the emails will be sent showing an attachment icon (little paperclip) when looking in the sent folder.

In addition, when the computer is I didn't send the e-mail from syncs the sent folder, there is no attachment icon shown on the machine syncing the sent e-mail.

I tested not using a signature and I can confirm that the attachment icon was not on e-mails sent without a signature that contains an image.
This is the same signature I was using in my POP3 e-mail setup, and I never experienced this issue.

Does anyone know why this happens, and how I can create an e-mail signature that doesn't cause the above behaviour?

My [pop3] emails also show that attachment symbol when I've included an image in them [I have just tested this with the email set in the Office 2007 Options ribbon to html & it's the same with it set as plain text and rich text.

In Office 2021, these choices are in the Format text ribbon, ... {at the right-hand end}, Message format.
They behave the same way in Outlook 2021 - all show an attachment icon in the email folder.

Denis

Try3 said:

My [pop3] emails also show that attachment symbol when I've included an image in them [I have just tested this with the email set in the Options ribbon to html & it's the same with it set as plain text and rich text.

Denis

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@Try3 - As per my original post when using the POP3 setup, the signature I still use never ever showed an attachment icon for sent e-mails without an attachment. See attached screenshot of my archived e-mails (as recently as last week) that show this wasn't happening.

But as of setting up IMAP settings from Monday this week, all this changed. It's really weird.

My testing was faulty.
I can now reproduce what you show when I use pop3 in Outlook 2007 & in Outlook 2021.
Has IMAP possibly changed something in your signature files themselves? The [not known by me] method by which the image is included in the signature files?
C:\Users\%UserName%\AppData\Roaming\Microsoft\Signatures
I don't think IMAP signatures are stored somewhere else because there's no mention of any change to their location in Find and transfer Outlook data files from one computer to another - MSSupport

Perhaps you have a pre-IMAP backup of the signature's rtf & htm files and its sub-folder where the image is stored so you can compare them all?


Denis

Try3 said:

My testing was faulty.
I can now reproduce what you show when I use pop3 in Outlook 2007 & in Outlook 2021.
Has IMAP possibly changed something in your signature files themselves? The [not known by me] method by which the image is included in the signature files?
C:\Users\%UserName%\AppData\Roaming\Microsoft\Signatures

Perhaps you have a pre-IMAP backup of the signature's rtf & htm files and its sub-folder where the image is stored so you can compare them all?

Denis

Click to expand...

On the laptop running Windows 10 when I deleted the POP3 to create the IMAP account the signature files were not affected. And since I didn't re-install the OS or MS Outlook 2021, I just had to select the same signature I used before when finishing my IMAP account setup.

So in my mind, this is the same pre-IMAP signature, unless I'm not understanding something correctly. The only machine that needed me to physically create a new matching signature was the desktop (running Windows 11) since that was a new build with new everything.

However, both machines are not doing this showing an attachment icon when sending e-mails that have no attachment, only because there is a signature included.

OverDose said:

However, both machines are not doing this showing an attachment icon

Click to expand...

You should be able to compare their rtf, htm, txt files & the subfolder between your computers to see what difference there is.

As long as you give the signatures different names in Outlook's Signatures...*** dialog you can copy them {rtf, htm, txt files & the subfolder} between your computers to see how the good signature behaves on the bad computer.

*** I have only been able to get to this dialog by opening a draft email then
and I have not been able to rename a signature outside of Outlook.

Denis

Try3 said:

You should be able to compare their rtf, htm files & the subfolder between your computers to see what difference there is.

As long as you give the signatures different names in Outlook's Signatures... dialog you can copy them between your computers to see how the good signature behaves on the bad computer.

Denis

Click to expand...

Well, the "good signature" is doing the exact same behaviour (i.e. creating an attachment icon), and the only commonality is the use of IMAP settings.

My suspicions lie with something to do with IMAP settings that makes this behaviour occur.

In the past (when on POP3) I would literally not even need to backup signatures when doing a fresh install on MS Suite or Windows, and once I imported my backed-up PST file, I would recreate a fresh signature by copying and pasting it from previously sent e-mails.

But the "good signature" on the not-new machine is also creating attachment icons.

Sorry, I thought your earlier post meant that one of them was still behaving as you wanted.
I don't have any other ideas.
It's possible that the change is deliberate. Perhaps corporate MSOffice customers complained that the lack of explicit identification as an attachment allowed such emails to bypass parts of their security scanning.

Best of luck,
Denis

Try3 said:

Sorry, I thought your earlier post meant that one of them was still behaving as you wanted.
I don't have any other ideas.

Best of luck,
Denis

Click to expand...

Oh well, let's wait and see. Perhaps there is a greater Mage than you or I who will swoop in and unpick the issue and leave us all marvelled at their stupendous stupendousness.

Thanks all the same for trying.

There's a very old discussion of this at Help! Every email I send has two unknown attachments - SlipStick
And Adding an Image to a Signature - SlipStick sub-heading Create a signature with a linked image describes adding an image link to a signature instead of an image. Perhaps that will make a difference? I've never tried doing that.

All the best,
Denis

Try3 said:

There's a very old discussion of this at Help! Every email I send has two unknown attachments - SlipStick
And Adding an Image to a Signature - SlipStick sub-heading Create a signature with a linked image describes adding an image link to a signature instead of an image. Perhaps that will make a difference? I've never tried doing that.

All the best,
Denis

Click to expand...

I had seen both of these links above, and neither of them helped with this phantom attachment icon issue.