Squash not allowed only explained after 2nd request to merge

### Is there an existing issue for this?

- [X] I have searched the existing issues

### Package ecosystem

pip

### Package manager version

_No response_

### Language version

python3.11

### Manifest location and content before the Dependabot update

_No response_

### dependabot.yml content

_No response_

### Updated dependency

_No response_

### What you expected to see, versus what you actually saw

As you can see in this screenshot, I asked dependabot to `squash and merge`. It waited for the CI to pass, I approved, and nothing happened.

Only when I asked it a second time did it update and say that squashes aren't allowed. I then was able to simply ask to merge and it did without a problem.

### Native package manager behavior

_No response_

### Images of the diff or a link to the PR, issue, or logs

_No response_

### Smallest manifest that reproduces the issue

_No response_