Well, I'm not sure about the exact titles all the time. But you can start your search on fanfiction platforms. Look for tags like 'tails', 'emotional', 'crying'. Some writers might focus on Tails' backstory, like his time as an orphan, and that could be a great source for crying - related fanfictions. You might also find some crossovers where Tails is put in a difficult situation in a different universe and cries as a result.
There is a fanfiction I heard about where Tails gets separated from his friends during a big battle. This makes him feel very alone and scared, and he starts crying. However, he then finds the inner strength to keep going. Another idea for finding 'tails crying' fanfiction is to check out the works of well - known Sonic the Hedgehog fanfiction authors. They often explore the emotional depth of characters like Tails and might have written something that fits this theme.
One popular 'tails crying' fanfiction might be 'Tails' Lonely Struggle'. It delves into Tails' feelings of isolation and the challenges he faces, which could lead to some emotional, crying moments. Another could be 'When Tails Lost Hope' where he experiences a great setback and his reaction involves crying. There are also fanfictions that explore his relationship with Sonic and how misunderstandings can make Tails break down in tears.