You enabled Telegram monitoring in Application File Access but detection does not work for file upload on MacOS systems.
DLP agent on MacOS systems.
Telegram application before uploading the file copies it first to its own temporary location and changes its extension.
Add monitoring path to Channel Filters in Agent Configuration:
/users/*/library/group containers/*.telegram/*/postbox/media/local-file*
This is the location where Telegram copies files before upload.