Newly matched 4th year med student. When to buy disability insurance?

[Dreamgiver]

Group policy is almost worthless, pretend it does not exist. Get an individual policy from one of the big 4 (or I believe 3 now that MetLife has left the market). Do not go with cheap no name (see AMA brochures) companies. Get the COLA and pay for the policy with after tax money. It will cost you somewhere around $1300/year for a resident's salary. When done with residency exercise the FPO to the maximum amount. Anesthesiologists do pay more. BE straightforward with the agent in order to avoid a potentially expensive mistake later and see if they will issue you a policy with the cheaper GS or IM year you will be doing. Congrats on matching!