I have a file with a retention time of 14 days based on our setup of the tagging. If we setup another tag with extended time of another 14 days should i setup another tag with the retention time of 28 days? since the files are deleted from the day they are created?
hello @Kevin4 welcome to the community 
I would recommend you test with trash data.
Especially take care of retention policies e.g. 14d policy does not apply if there is another tag