On 32 button DTP/DTU at 24-gage, 360'; 16-button DTP/DTU 450'; 8-button 600'.

Increasing wire size will decrease resistance and increase loop length. Length can also be increased by "doubling up" pairs, i.e. twist tips of two pairs and rings of two pairs together at each end, then treat it as one pair.

At the extremes of loop length, phones will take a long time to come up.

Maximum recommended for an analog extension in general is around 1500' from the port, though it may work beyond that, but with decreased ringing and decreased handset volume. I believe that NEC recommends a maximum of 200' from the port for an analog.