Unreliable Copy and Paste

Sometimes when I copy a bit of text and then try to paste it, I end up pasting the previous item from the clipboard; it's as if the last "copy" command never overwrote the previous characters in the clipboard. Then when I try again, it works. But this means four steps at what should be a quick one-two process. For example:

  1. I copy the words "Keyboard Maestro"
  2. I paste the words "Keyboard Maestro" without incident
  3. I copy the number "(555) 999-4444"
  4. I attempt to paste the phone number, but a paste command results in "Keyboard Maestro."
  5. I copy the phone number again.
  6. I paste it successfully.

I figure it has to be something with the multiple tools I have loaded, so I'm trying to condense. I have TextExpander, Keyboard Maestro, the "Paste" app from https://pasteapp.io/, and PopClip. That's 4 that share clipboards.

I know I can abandon "Paste" by learning how to use the clipboard switcher in KM correctly. PopClip I use all the time every day so that has to stay. TextExpander can go, I just need to find the best way to import those few dozen abbreviations - I posted a question in the macro library but apparently that was the wrong place since it was such an old thread. Any ideas how I can do some snooping to find which app is the culprit? Even if I eliminate some factors, the problem could remain. I'd like to sniper the issue instead of the shotgun approach.

Is this with automated copy actions in KM, or manual copying?

MS Office can be a culprit as it likes to put multiple data types on the clipboard afaik.

Keyboard Maestro shouldn't affect copying items, not unless you have a macro that is triggered. Keyboard Maestro’s reading of the clipboard after a copy can affect some applications. But this doesn't sound like that sort of issue.

I'd be very surprised if it was TextExpander.

I don't know about Paste so I can't make any comments on it. PopClip does some things that I suspect require poking around in places that apps aren't supposed to which could be an issue. But I don't know of anything like you describe.

Debugging sporadic failures is always going to be hard. For all you know it is some other app that is left over with something installed you've forgotten about. Other than trying to uninstall the apps and see if it reappears, there isn't much else to suggest. And just disabling apps does not necessarily remove all of their components. For Keyboard Maestro, quitting Keyboard Maestro and the Keyboard Maestro Engine entirely removes it from influencing the system, but sometimes apps install extra components or patches that may still be active even if you think they are disabled, which can mean you think an app is not the issue when it is.