Commit that causes the regression:
commit 33ec3e53e7b1869d7851e59e126bdb0fe0bd1982
Author: Jan Kara <j...@suse.cz>
Date:   Thu May 16 16:01:27 2019 +0200

    loop: Don't change loop device under exclusive opener
    
    Loop module allows calling LOOP_SET_FD while there are other openers of
    the loop device. Even exclusive ones. This can lead to weird
    consequences such as kernel deadlocks like:
    
    mount_bdev()                            lo_ioctl()
      udf_fill_super()
        udf_load_vrs()
          sb_set_blocksize() - sets desired block size B
          udf_tread()
            sb_bread()
              __bread_gfp(bdev, block, B)
                                              loop_set_fd()
                                                set_blocksize()
                - now __getblk_slow() indefinitely loops because B != bdev
                  block size
    
    Fix the problem by disallowing LOOP_SET_FD ioctl when there are
    exclusive openers of a loop device.
    
    [Deliberately chosen not to CC stable as a user with priviledges to
    trigger this race has other means of taking the system down and this
    has a potential of breaking some weird userspace setup]

Seems like it solves a race so I'll raise the issue to the commit
author.

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https://bugs.launchpad.net/bugs/1836914

Title:
  Doing multiple squashfs (and other loop?) mounts in parallel breaks

Status in linux package in Ubuntu:
  Confirmed

Bug description:
  On a system running a 5.2 kernel, doing a large number of mounts of
  squashfs filesystems in parallel results in the mounts getting out of
  sync with their backing devices.

  To reproduce,

  https://paste.ubuntu.com/p/VCpzGxvy6h/

  this breaks people with ~40 snaps (easily achievable given snapd
  leaves up to 3 previous revisions of snaps mounted at any given time,
  so a person with ~13 snaps that get updated often will hit this
  number).

  ProblemType: Bug
  DistroRelease: Ubuntu 19.10
  Package: linux-image-5.2.0-8-generic 5.2.0-8.9
  ProcVersionSignature: Ubuntu 5.2.0-8.9-generic 5.2.0
  Uname: Linux 5.2.0-8-generic x86_64
  ApportVersion: 2.20.11-0ubuntu5
  Architecture: amd64
  AudioDevicesInUse: Error: command ['fuser', '-v', '/dev/snd/seq', 
'/dev/snd/timer'] failed with exit code 1:
  CurrentDesktop: ubuntu:GNOME
  Date: Wed Jul 17 15:11:15 2019
  InstallationDate: Installed on 2019-07-17 (0 days ago)
  InstallationMedia: Ubuntu 19.10 "Eoan Ermine" - Alpha amd64 (20190716)
  IwConfig:
   ens3      no wireless extensions.
   
   lo        no wireless extensions.
  Lsusb: Error: command ['lsusb'] failed with exit code 1:
  MachineType: QEMU Standard PC (i440FX + PIIX, 1996)
  ProcFB: 0 qxldrmfb
  ProcKernelCmdLine: BOOT_IMAGE=/boot/vmlinuz-5.2.0-8-generic 
root=UUID=9618ebbb-955d-4daf-b29a-37162ec7821a ro quiet splash vt.handoff=7
  RelatedPackageVersions:
   linux-restricted-modules-5.2.0-8-generic N/A
   linux-backports-modules-5.2.0-8-generic  N/A
   linux-firmware                           1.180
  RfKill:
   
  SourcePackage: linux
  UpgradeStatus: No upgrade log present (probably fresh install)
  dmi.bios.date: 04/01/2014
  dmi.bios.vendor: SeaBIOS
  dmi.bios.version: Ubuntu-1.8.2-1ubuntu1
  dmi.chassis.type: 1
  dmi.chassis.vendor: QEMU
  dmi.chassis.version: pc-i440fx-xenial
  dmi.modalias: 
dmi:bvnSeaBIOS:bvrUbuntu-1.8.2-1ubuntu1:bd04/01/2014:svnQEMU:pnStandardPC(i440FX+PIIX,1996):pvrpc-i440fx-xenial:cvnQEMU:ct1:cvrpc-i440fx-xenial:
  dmi.product.name: Standard PC (i440FX + PIIX, 1996)
  dmi.product.version: pc-i440fx-xenial
  dmi.sys.vendor: QEMU

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