Hey there rdosh,
We'd like to help however we can. You mentioned Safari opens to a new window, which is the default setting, but if you'd like to change this, you can do so by opening Safari, then clicking on Safari > Preferences > Safari opens with:, then select your preferred setting.
To start on the issue occurring with Reopen All Windows from Last Session under the History menu, let's confirm the following:
- When did this first start to occur?
- If you test opening three tabs, then quit/open Safari, does the same issue occur?
- Have you already tried a restart of your Mac? Check out the section 'Restart' here: Log out, sleep, wake, restart, or shut down your Mac
- If you have a compatible Mac model, the latest version is macOS 12.1. While it's not necessary to upgrade your macOS, we do recommend making sure to have the latest updates for your currently installed macOS version. We see you have macOS 10.13, but the latest version for that macOS is 10.13.6. You can verify this by clicking on the Apple logo at the top left corner of the screen, then on ‘About This Mac’. Here's how to first Back up your Mac with Time Machine, and afterwards, here's How to update the software on your Mac.
Cheers!
