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In Indian railways, the chances for getting a ticket confirmed from waiting list depends on several factors.
1. Which route are you traveling:
There are some routes where you will struggle to get a reservation, and there are routes, where you can reserve ticket even on the day of journey.
2. What season are you traveling in:
As India is a land of festivals, there are several festiv seasons in an year (Most of the day is a festival somewhere in India), like dassara, holi, christmas, janmashtami, ganesholtsav, Onam, Vishu, Eid, and a hundred of them. You should not expect getting a confirmed ticket easily during these days.
3. What class are you traveling in:
In most of the trains, traveling in general class and sleeper class is tough due to the number of travelers. But you can easily get a reservation on an AC coach.
4. Which train are you traveling in:
Most of the passengers will be frequent travelers and they prefer to travel in their favorite train (According to time of travel, facilities,etc). As there are wide variety of trains here, you'll have to chose according to your comfort level.
And in India, you'll need some luck after all ;)