IPad – Using the iPad Pro with Apple digital AV Adapter and headphone jack adapter

It sounds like a hardware problem in the jack. If you can put pressure on the external part of the plug and change it: cause static or breakup it's probably a hardware problem in the jack.

If you had said you only tried one set of headphones then I'd have said it's probably a problem in the headphone plug but if it's multiple phones and speakers then it's probably the jack.

There's a sensor in that jack that monitors if something's in it or not to switch off the internal speakers. The if there's continuous sound, just switching from internal to external the problem may be that sensor. If the sound cuts out from both internal and external once in a while it's probably the jack.

If the MacBook Pro is still under warranty I'd have Apple look at it, they'll swap motherboard to make it right if it's a hardware problem at no cost to you.

I can recommend the 'SoundSticks I' from Harman Kardon, a very good 3-way Sound System. The first Generation had an USB-Interface, the later Models had the usual Headphone Jacks. You can get it from E-Bay, usually for less than 80$.

One important thing: You cannot use them on a USB-Hub, you have to connect them directly to you machine.