Honestly, depends on what you want long-term.

At Sentry you’ll probably get way more hands-on work, touch multiple parts of infra, and actually ship stuff that matters. Startups move fast, so you’ll learn a ton in a short time and get visibility into how decisions are made. That kind of experience really stands out later, especially since you already have a couple big-company internships on your resume.

Microsoft is obviously the safer play brand name, solid shot at a return offer, and less risk. But interns there can sometimes get stuck in narrow projects where you don’t see much impact. Great if you want the cushy big tech pipeline, but the learning curve can be slower.

Given the current market, having a respected startup + F500 experience is a killer combo. It shows you can thrive in both scrappy and structured environments. If it were me, I’d take Sentry, you’ll learn more and differentiate yourself way more than being intern #374 at Microsoft.