I have been using a Dell xps 15 9560 laptop with Ubuntu 16.04 since the 9560 was released. In December of 2018, I received two Dell U2717D monitors and have been connecting them to my laptop so that I could have three displays (my laptop's screen plus the two monitors). I have been using a USB-C to Displayport connection for one monitor and just straight HDMI for the other. This has been working well for me up until this morning (nearly three months after receiving the monitors).
This morning, as usual, I opened my laptop, plugged in both monitors, and switched them on. Everything was seemingly normal except my computer's background was not appearing on any of my displays, though I could go on the internet and open all other applications just fine (though things were a bit glitchy). I attributed this to standard Linux-related headaches, so I decided to restart my computer. Now here is where things get interesting. My computer booted up as normal and everything was displaying on all three monitors during bootup but, once I logged in, both external monitors said that they were not receiving signal from my laptop. I decided I should unplug both and plug them back in, as you do, to see if that would change anything. Once I unplugged the HDMI cable, my second monitor popped up its normal display. I plugged the HDMI cable back in, both monitors displayed the same "no ____ signal from your device" again. I then unplugged the USB-C connection and the HDMI-connected monitor popped its normal display back up. I plugged the USB-C cable back in and, yet again, I was met with "no ____ signal from your device" on both monitors yet again.
At this point I was mildly frustrated and I looked in the display settings and it showed only one external monitor plugged in (keep in mind they are both plugged in at this time) and it was set to "off" so I toggled it to "on" and nothing happened. Using xrandr, it shows that both monitors are connected. Now here is where things get even stranger. I decided to just restart my computer once more and, during the restart process, both monitors immediately displayed their normal contents. Even on boot, both external monitors were displaying their normal contents. I finally made it to the login screen, typed in my password and pressed enter (feeling accomplished at this point for doing nothing). Immediately upon signing in, both external monitors immediately gave me their "no ____ signal from your device" messages once again. Now I am here and wondering if anyone knows what could possibly be the cause of this. I did quite a bit of searching online but it seems that no one has run into this specific problem.
A side note, I do not know if it matters, but I was able to connect my phone to my computer via USB-C with the HDMI monitor also connected and everything worked just fine. I am literally only running into problems when I am signed in.
Laptop: Dell xps 15 9560
OS: Ubuntu 16.04
Problem: Have two external monitors (both Dell U2717D), one connected via HDMI and the other connected via USB-C to Displayport. Setup worked for three months, then, randomly, stopped working this morning when both are plugged in. Both work fine during shutdown and boot sequence but, once I login, I can only get one to work at a time.
Thank you in advance for any insights/assistance.
Edit: For what it is worth, I am using kernel 4.8.0-41-generic