It's sad when there are many misdirected mails (6)
I believe the answer is:
dismal
'it's sad' is the definition.
(thesaurus)
'many misdirected mails' is the wordplay.
'many' becomes 'd' ().
'misdirected' indicates anagramming the letters (I've seen this in other clues).
'mails' is an anagram of 'ismal'.
'd'+'ismal'='DISMAL'
'when there are' acts as a link.
I am not very happy about this link. Some or all of it may belong to another bit of the clue.
Can you help me to learn more?
(Other definitions for dismal that I've seen before include "Gloomy, bleak" , "Depressing; dreary" , "Miserable" , "down in the dumps" , "pitifully bad" .)