Odd behavior/delay in Preview jpg resizing (Mac OS Ventura)

I usually resize my iPhone photos when sending them as attachments in an email when working on my MBPro
I had a snapshot to send to a customer support via email.
I resized it in Preview and renamed it, then proceeded to compose an email.

After about ten minutes when navigating in gmail to attach the file I noticed the jpg still had its
original name.
On the desktop the file was properly renamed.
I opened the file and quit the app.
When proceeding to attach the file again, it had the correct name, however the file was grayed out.
Not knowing exactly what to do I experimented by clicking and dragging the file to create a copy.
When proceeding again to attach the file I now had the two files properly named.
This sort of indicates that it took ten minutes for Preview to finish the edit in the first file … or something …

Any thoughts on this?

No idea, but it’s not entirely clear how you’re resizing (crop vs resize) or renaming (saving, exporting, sharing) the image.

I just opened an image in Preview on Ventura, did Adjust Size and then Save(d) As a new file name and it was instant.

Normally I wouldn’t do this sort of thing for email. I drop an original image into Mail app and choose the size before sending - normally ‘medium’ is adequate but Actual Size is good for max quality.

my method is basically
image > Preview > Tools > Adust Size > 50% and rename in the Name panel while image is open.

I have not optimally configured my phone particularly well for photos so I actually get a whole variety of jpeg, and HEIC sizes
Thus I have been always been resizing sort of as a courtesy to recipients not to have to receive bulky attachments.
I’m not actually using Mail
I only just recently noticed the drop in function with GMail, however both my personal and work suite gmail accounts do not offer a resize function at the drop point

and, by the way, this phenomenon may have been a one-off … I have not been able to duplicate the symptom

I now have an actual example to illustrate the weird phenomenon described above
I exported a HEIC photo from my phone to a renamed/resized jpg
Please note screenshot that shows the exported file on the desktop correctly
However, in the gmail queue for adding as an

attachment, the file shows up only with the original file name and type (after about 10 or 15 minutes having exported the image file)

for clarity, the original image 6642 HEIC file was long in the trash by the time I was attempting to attach the jpg

Sorry to be a nag about this, but my experience is that Ventura has a real bug with regard to attaching files on the desktop at websites, or via email.
This version is an attempt to upload a screenshot to my healthcare provider via their website upload protocol
Please note in the attachment here two screenshots exist on the desktop, but the upload protocol has them grayed out and cannot be selected in order to trigger the blue Upload button
Somewhat ironically, I suppose, there is no issue at tidbits website uploading the screenshot below

If you Get Info on those screen shots, are they .PNG files?

Perhaps your healthcare provider’s web site doesn’t like .PNG files - which is the default for macOS screen shots? Is it possible that they’re telling macOS to look for JPEG or PDF files when asking for files to upload?

Well, you are right on that, I sort thought about that just after writing the update here,
So I guess I am back to the previous observations in my post.
Please note the previous screenshot which shows that in Gmail (Safari/Firefox) the file desired for attachment has the preferred file type and is on the desktop, But in the attachment queue only the original HEIC file (which was actually in the trash at that point) shows up, and the jpg does not display in the attachment queue
so I still think something funny’s going on :upside_down_face:

It may have the right file type from the Mac’s standpoint, but does it have a .jpg extension? There are cases that I’ve found where non-Mac utilities/websites want file extensions “in the interest of cross-platform, least common denominator”.

Just to clarify the first screenshot.
On the desktop there is a .jpg renamed “random …” which was created by exporting from the original photo img_6642.heic
At the time I was trying to attach the .jpg (extension appended, see photo) to an email
the file in the queue to attach files shows up as the old original HEIC file … which, by the way, was actually in the trash!.
Please note that the .jpg was on the desktop and does not show up in the queue in any manner … grayed out or otherwise, for attaching to the email