Programs won't add to Startup

Ok, so I was having some issues with my previous build (Insider), and with the help of a hard disk crashing, I went and did a full wipe and a clean install.

Unfortunately, some of my programs refuse to add to startup even when the "Start with Windows" option is checked. I've tried completely removing the programs and re-installing and they simply will not start with Windows like they should.

Aside from manually overriding the situation, (which is a workaround, and not a fix), any ideas on how to truly resolve this?

Have you tried opening these programs by right clicking and selecting "Run as Administrator" when you attempt to apply the setting for run at startup? Maybe they also need to be installed by running the setup via the "Run as an administrator" route.

philc43 said:

Have you tried opening these programs by right clicking and selecting "Run as Administrator" when you attempt to apply the setting for run at startup? Maybe they also need to be installed by running the setup via the "Run as an administrator" route.

Yes, that was my first thought. Steam doesn't like to be run as admin, but it doesn't seem to matter either way. Some programs haven't had an issue while others just won't add. It's mind boggling.

Well, have an update.

Completely removed Steam and Skype (the two programs that are having the main issues atm), and also removed all locally stored data for the programs.
Then after finally receiving the 14257 insider build, proceeded to install it, then re-installed my two programs.

On the plus side, Skype finally remembers my login data and basic camera settings so I'm not prompted every single time I start it up anymore.
Unfortunately, neither Steam, not Skype will start with Windows.

Another oddity. Now they are both listed in the startup programs list. But they absolutely do not start with Windows.