Install.packages is reporting success, but my package isn't updating.

Hello, I have a question on Installing packages.

I am currently attempting to install an internally developed package from RStudio Package Manager as part of a Continuous Integration Build Plan. I have confirmed that the Package is picked up from the repository. As well as I have confirmed that in other development environments the package updates successfully, and more importantly, the update sticks.

In one of our development environments I can see the CI job say that my package has been installed successfully. Yet, when I go to the server to confirm that fact, running a packageVersion('') it shows my package on it's older version it was trying to update from.

Further complicating things is then when I run my CI plan again on the server, the update goes through again and the update is shown on the server when I run an packageVersion()

TLDR: One server needs to have an Install.package run on it twice in order for an update to stick. Has anyone ever ran into this before? Or does anyone have any debugging or troubleshooting tips to audit the install process? my apologies I do not have any output or code at the moment. I am mainly looking for how I could unravel the install process to understand exactly what is going on.