Cannot paste screenshots into a Message using context menu since Big Sur upgrade

changing the format of the screenshot to jpg worked for me. Use the below command in terminal

defaults write com.apple.screencapture type jpg

Talked to Apple support. This ability was deprecated in Big Sur.

They mentioned to submit feedback to let the product managers know we’d like this ability back.

https://www.apple.com/feedback/

Log into another vanilla admin user account, Set up users, guests, and groups on Mac,  and see if the problem persists. (This tells us if the problem is limited to your user account or is system wide).

I just went in to my Screenshot preferences and reset them to save to the Clipboard and was able to add a screenshot to a Message. So it works with Big Sur 11.1.

Download and run Etrecheck. Etrecheck is a diagnostic tool that was developed by one of the most respected users here in the ASC and recommended by Apple Support  to provide a snapshot of the system and help identify the more obvious culprits that can adversely affect a Mac's performance.

Copy the report

and use the Additional Text button to include the report in your reply.

IMPORTANT:

Before running Etrecheck assign Full Disk Access to Etrecheck in the Etrecheck's Privacy preference pane so that it can get additional information from the Console and log files for the report:

Also click and read the About info to further permit full disk access.

Then we can examine the report and see if we can determine what might be causing the problem.

mikebirminghamuk,

What happens when you test the issue while in safe mode? Are you then able to paste into Messages?

How to use safe mode on your Mac - Apple Support

"Safe mode prevents your Mac from loading certain software as it starts up, including login items, system extensions not required by macOS, and fonts not installed by macOS. It also does a basic check of your startup disk, similar to using First Aid in Disk Utility. And it deletes some system caches, including font caches and the kernel cache, which are automatically created again as needed."

Regards.

Press and hold the CONTROL key as you take the screenshot and continue to hold the CONTROL key as you click CAPTURE. Then, click inside the text message and press COMMAND + V. This has been working for me on my Macbook Pro (2019).

An easy workaround is save the screenshot to the Desktop and drag it into the Message app.

I made a "vanilla" admin account and found that it has the same problem. If I take a screenshot it can be pasted into a Note, onto the Desktop, into Word or an email but the paste option is greyed out when I try to paste it into iMessage. Text that is copied can be pasted into iMessage though. It appears that screenshots are the issue.

Press and hold the CONTROL key as you take the screenshot and continue to hold the CONTROL key as you click CAPTURE. Then, click inside the text message and press COMMAND + V. This has been working for me on my Macbook Pro (2019).

Hello mikebirminghamuk,

Thank you for using Apple Support Communities!

We understand from your post that you are unable to paste a screenshot to a Message but can paste it to other applications like Pages. Try using the Control key when you take the screenshot as described below and see if you can then paste it into your messages.

Take a screenshot on your Mac - Apple Support

"To copy a screenshot to the Clipboard, press and hold the Control key while you take the screenshot. You can then paste the screenshot somewhere else." 

Best Regards.

I have the exact same problem on my MacBook Pro. I can take a screenshot and paste into a Word document but the "paste" option is greyed out for pasting into messages.

Hi, any resolution to this issue, i have the same problem: https://discussions.apple.com/thread/252304470?page=1

I have this same issue. I can paste into other programs but not Messages. It makes it difficult to text a screen shot to a contact. Might it have something to do with the format set for the screen shot (e.g. pdf)?

I have the same issue since recently updating to Big Sur. When I press command>shift>4 I get the crosshair, drag to cover the area in question, then release to take the screenshot. The computer makes the normal camera shutter sound, but it also has another simultaneous sound, like a defective function sound. Like other users, I am able to press command>v to paste, but when I two-finger-tap to give me the paste option, only COPY is hi-lighted as an available option.