What could cause this scenario? I can see the veeam guest helper logs successfully claiming that all relevant (Full recovery mode) DBs have truncated as below (db2/db3 are simple mode):
22/05/2017 18:39:22 1512 Database tempdb: skipped transaction log truncation.
22/05/2017 18:39:22 1512 Database model: transation logs have been truncated.
22/05/2017 18:39:22 1512 Database msdb: skipped transaction log truncation.
22/05/2017 18:39:22 1512 Database <db1>: transation logs have been truncated.
22/05/2017 18:39:22 1512 Database <db2>: skipped transaction log truncation.
22/05/2017 18:39:22 1512 Database <db3>: skipped transaction log truncation.
22/05/2017 18:39:22 1512 Database <db4-didn't-truncate>: transation logs have been truncated.
22/05/2017 18:39:22 1512 Database <db5-didn't-truncate>: transation logs have been truncated.
DB1 did truncate as expected & the DBA was able to shrink this TL (it had grown to 40Gb over a period of time)
DB's 4 & 5 would expect to have a huge amount of white space now but don't.
Oh, & I just spotted a typo in your log generation "transation" rather than "transaction"
