Redmine

Step to reproduce
1. Create custom field named deadline with type 'date'
2. Set Default value to 2100-01-01 (far future)
3. Create one task and set 'deadline' to tommorow
4. Goto filters and set sorting by 'deadline' field
-what you will see
New task will be placed at the end of queue
-what expected to see
new task will be placed as first task in queue.

NB! If you updated every exist task in your project then 'deadline' field will be reseted to default value and sorting by 'deadline' will work properly but it's impossible to do that automatically :(