The free space checks for /usr seem a bit strange:

2018-08-09 19:17:15,431 DEBUG Free space on /: 1110441984
2018-08-09 19:17:15,431 DEBUG Free space on /usr: 2819907584
2018-08-09 19:17:15,432 DEBUG Free space on /var: 3585171456
2018-08-09 19:17:15,432 DEBUG Free space on /boot: 301889536
2018-08-09 19:17:15,432 DEBUG Dir /var/cache/apt/archives mounted on /var
2018-08-09 19:17:15,432 DEBUG Free space on /tmp: 10716753920
2018-08-09 19:17:15,432 DEBUG Free space on /home: 2221584384
2018-08-09 19:17:15,432 DEBUG Dir /tmp mounted on /tmp
2018-08-09 19:17:15,432 DEBUG fs_free contains: '{'/': 
<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6bd30>, '/usr': 
<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6bd68>, '/var/cache/apt/archives': 
<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6beb8>, '/boot': 
<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6be10>, '/var': 
<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6beb8>, '/home': 
<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6bef0>, '/tmp': 
<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6bcf8>}'
2018-08-09 19:17:16,690 DEBUG linux-image-4.15.0-30-generic (new-install) added 
with 20705456 to boot space
2018-08-09 19:17:19,295 DEBUG dir '/var/cache/apt/archives' needs '3474732250' 
of '<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace 
object at 0x7f9460e6beb8>' (3585171456.000000)
2018-08-09 19:17:19,296 DEBUG dir '/usr' needs '-3102259200' of 
'<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6bd68>' (2819907584.000000)
2018-08-09 19:17:19,296 DEBUG dir '/usr' needs '52428800' of 
'<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6bd68>' (5922166784.000000)
2018-08-09 19:17:19,296 DEBUG dir '/boot' needs '121070520.8' of 
'<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6be10>' (301889536.000000)
2018-08-09 19:17:19,296 DEBUG dir '/tmp' needs '5242880' of 
'<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6bcf8>' (10716753920.000000)
2018-08-09 19:17:19,296 DEBUG dir '/' needs '10485760' of 
'<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6bd30>' (1110441984.000000)
2018-08-09 19:17:19,296 DEBUG dir '/tmp' needs '0.0' of 
'<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6bcf8>' (10711511040.000000)
2018-08-09 19:17:19,296 DEBUG dir '/usr' needs '0.0' of 
'<DistUpgrade.DistUpgradeCache.MyCache.checkFreeSpace.<locals>.FreeSpace object 
at 0x7f9460e6bd68>' (5869737984.000000)

Could you provide some information regarding how your disk and
partitions are setup? Thanks in advance!

** Changed in: ubuntu-release-upgrader (Ubuntu)
   Importance: Undecided => High

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https://bugs.launchpad.net/bugs/1786484

Title:
  Updater doesn't check size of partitions.

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