Sounds like you have two bugs.

Asking for the password twice is bug 1765261.

But it sounds like you also have a crash causing your lost session so...

-----

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please follow these steps:

1. If you are not running a future development release of Ubuntu then apply the 
workaround from bug 994921.
2. If you are running the Ubuntu Stable Release you might need to enable apport 
in /etc/default/apport.
3. If the crash is in Xorg then uncomment this option from 
/etc/gdm3/custom.conf:
   # Additionally lets the X server dump core if it crashes
   #Enable=true
4. Reboot.
5. Reproduce the crash.
6. Look in /var/crash for crash files and when found, run:
   ubuntu-bug /var/crash/YOURFILE.crash
7. Add a comment here telling us the ID of the new bug that was created in step 
6.

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** Changed in: xorg-server (Ubuntu)
       Status: New => Incomplete

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You received this bug notification because you are a member of Desktop
Packages, which is subscribed to xorg-server in Ubuntu.
https://bugs.launchpad.net/bugs/1771716

Title:
  Resuming resets my session

Status in xorg-server package in Ubuntu:
  Incomplete

Bug description:
  I installed 18.04 from scratch a day after it got released.

  Twice per day I close the lid of my laptop and open it again after.
  Usually it immediately asks me for the password and brings me back to
  what I was doing.

  But 3 times so far, it took a minute before showing me a login screen
  (like if I had not yet a session) asking me to choose my user (there
  is only one user), then enter my password. It then starts to load...
  and asks me for my password AGAIN. Then it shows my desktop, but
  everything I was doing before is gone, no more open windows. When I
  start Firefox it asks me whether I want to restore my tabs. When I
  open Byobu it shows my tabs as I left them.

  ProblemType: Bug
  DistroRelease: Ubuntu 18.04
  Package: xserver-xorg-core 2:1.19.6-1ubuntu4
  ProcVersionSignature: Ubuntu 4.15.0-20.21-generic 4.15.17
  Uname: Linux 4.15.0-20-generic x86_64
  ApportVersion: 2.20.9-0ubuntu7
  Architecture: amd64
  BootLog: Error: [Errno 13] Permission denied: '/var/log/boot.log'
  CompositorRunning: None
  CurrentDesktop: ubuntu:GNOME
  Date: Thu May 17 11:27:19 2018
  DistUpgraded: Fresh install
  DistroCodename: bionic
  DistroVariant: ubuntu
  DkmsStatus: virtualbox, 5.2.10, 4.15.0-20-generic, x86_64: installed
  ExecutablePath: /usr/lib/xorg/Xorg
  ExtraDebuggingInterest: Yes
  GraphicsCard:
   Intel Corporation HD Graphics 5500 [8086:1616] (rev 09) (prog-if 00 [VGA 
controller])
     Subsystem: Lenovo HD Graphics 5500 [17aa:2223]
  InstallationDate: Installed on 2018-04-29 (17 days ago)
  InstallationMedia: Ubuntu 18.04 LTS "Bionic Beaver" - Release amd64 (20180426)
  MachineType: LENOVO 20CKCTO1WW
  ProcKernelCmdLine: BOOT_IMAGE=/vmlinuz-4.15.0-20-generic 
root=/dev/mapper/ubuntu--vg-root ro quiet splash vt.handoff=1
  SourcePackage: xorg-server
  UpgradeStatus: No upgrade log present (probably fresh install)
  dmi.bios.date: 08/20/2015
  dmi.bios.vendor: LENOVO
  dmi.bios.version: N11ET34W (1.10 )
  dmi.board.asset.tag: Not Available
  dmi.board.name: 20CKCTO1WW
  dmi.board.vendor: LENOVO
  dmi.board.version: SDK0J40709 WIN
  dmi.chassis.asset.tag: No Asset Information
  dmi.chassis.type: 10
  dmi.chassis.vendor: LENOVO
  dmi.chassis.version: None
  dmi.modalias: 
dmi:bvnLENOVO:bvrN11ET34W(1.10):bd08/20/2015:svnLENOVO:pn20CKCTO1WW:pvrThinkPadT550:rvnLENOVO:rn20CKCTO1WW:rvrSDK0J40709WIN:cvnLENOVO:ct10:cvrNone:
  dmi.product.family: ThinkPad T550
  dmi.product.name: 20CKCTO1WW
  dmi.product.version: ThinkPad T550
  dmi.sys.vendor: LENOVO
  version.compiz: compiz N/A
  version.libdrm2: libdrm2 2.4.91-2
  version.libgl1-mesa-dri: libgl1-mesa-dri 18.0.0~rc5-1ubuntu1
  version.libgl1-mesa-glx: libgl1-mesa-glx 18.0.0~rc5-1ubuntu1
  version.xserver-xorg-core: xserver-xorg-core 2:1.19.6-1ubuntu4
  version.xserver-xorg-input-evdev: xserver-xorg-input-evdev N/A
  version.xserver-xorg-video-ati: xserver-xorg-video-ati 1:18.0.1-1
  version.xserver-xorg-video-intel: xserver-xorg-video-intel 
2:2.99.917+git20171229-1
  version.xserver-xorg-video-nouveau: xserver-xorg-video-nouveau 1:1.0.15-2

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