AVR-Ada Wiki
Ada cross compiler and libraries for AVR µCs
Status: Beta
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rolf_ebert
Jan found a newish in circuit debugger that is very cheap to build and works like a charm:
https://github.com/dcwbrown/dwire-debug
He uses it on a attiny441. It is quite liberal, as long as there is a dwire facility on the chip.
The is a facility to use it with gdb.
The only issue is that you have to program a fuse with avr-dude to enable dwire, but even that is not hard to incorporate. 5 serial port lines do everything.