Communication Breakdown; Time Pressure
Deviation / Discrepancy - Procedural FAR; Deviation / Discrepancy - Procedural Published Material / Policy
Equipment / Tooling; Human Factors; Weather
Took over [a] position and shortly thereafter MDW went below minimums. 2 aircraft entered the hold a 3rd was sent back to [departure airport] and another diverted to ZZZ prior to entering the hold. Also at this time I was having issues with AUS and BNA convective weather and possible diverts as well.SOD (Supervisor on Duty) requested [flight] divert to [ZZZ2 a nearby airport]. Aircraft had 45 minutes of divert fuel on board and ZZZ3 as the alternate. In the process of trying of using the reroute tool swift crashed. This happened at absolutely the worst time. Numerous ACARS messages and calls coming in. Asked my pod mates for help as well.Once [software] was rebooted I attempted to work on a reroute again and [software] crashed for the second time. I had informed [flight] to add ZZZ2 as an alternate; gave him the info and told him to divert to ZZZ2. TAF was showing 400/2 for ZZZ2. In the confusion I didn't realize the METAR at ZZZ2 was showing 300/1; below alternate minimums. I changed [the flights] destination to ZZZ2 and again with the workload and confusion of [software] crashing I neglected to add ZZZ4 as the alternate for ZZZ2. This was by far the busiest I've been and to lose my main tool in the heat of the battle was very stressful.
Dispatcher comments about the issues with their company's flight management system.