Customer wanted a photo of an item and I cannot upload photos in messaging.
It has not been working all day. Still not able to do it.
I had a similar issue. You might find an answer in the link here.
3 days later and it still won't work
@jewelryandthings2
On Etsy Help Center, under "How to Send Messages to Buyers" tab, it says:
How to attach files to Messages
To attach files:
The files can be up to 10,000 x 10,000 pixels or 100MB.
There's also an area at the bottom to contact support.
If nothing else, since you're a star seller, maybe you'd have better luck sending them an email from your main page.