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What Happens When You Leave Microsoft

Microsoft was my first job out of college and after 8 wonderful years, I decided it was time for a new challenge. As it was the first time I’d actually be quitting my job, I didn’t precisely know what to expect so I thought I’d document my experience, but the below likely applies to other companies as well:

Before Resigning

  • Rewards. Full-time employees as of 6/30 are eligible for annual rewards, so if you are planning to leave during that time frame, it might be financially wiser to wait before giving notice.
  • Stock Awards. Take into consideration your vest dates (typically 8/31) when determining your resignation date.
  • 401K. Microsoft’s 401K match is first-in-class. As my new employer’s 401K program wasn’t as great, I decided to max out my yearly contribution before leaving Microsoft.
  • StayFit. If you elected the StayFit benefit, make sure to use it before you leave.
  • HRWeb Checklist. There’s a checklist available on HRWeb that you can go through that’ll walk through some other items like getting copies of your paystub, making sure your address is up-to-date, etc. Microsoft.


  • Two Weeks Notice. There is no legal obligation for you to give two-weeks notice, but unless you enjoy burning bridges, try to give your manager/team sufficient notice of your intention to quit. In my situation, I didn’t want to jeopardize my bonus or stock vest so waited until 9/1 before giving formal notice to my manager.
  • Garden Leave. Thanks Lilian for expanding my vocabulary – garden leave is British vernacular and is a nicer way of saying, “Thanks for your years of service, we don’t trust you anymore so we’re going to revoke your access immediately, but in return you can get 2 weeks paid vacation”. When you resign, your manager will likely ask what’s in store for you next. If you choose to share where you’ll be going, your manager will be obligated to pass that information along to HR. If HR deems that you are leaving for a competitor, you should expect garden leave.
  • Pack your Things. Particularly if you expect you’ll be awarded with garden leave, you may not get a chance to collect your things as you’ll likely get walked out of the building shortly after giving notice.
  • Goodbye. Draft a goodbye email as you may not have a lot of time to announce your departure particularly if you will be receiving garden leave.
  • Making it Official. When you resign, there’s a simple HR tool that you fill out denoting when you wish your final day as a blue badge will be. Note that your manager has the ability to change this day to something earlier (possibly something later?). Once your manager accepts your resignation through the tool, it’ll kick off whatever HR workflow to determine if you should be awarded garden leave and such.

After Resigning

  • Benefits. Medical/Dental/Vision/Legal benefits will terminate on the last day of employment. For Medical and Dental, you will have the option to elect for COBRA coverage. A week or so after your last day, you should receive a letter in the mail explaining your options for COBRA.
  • Legal (ARAG). If you have an ongoing case with ARAG, as long as you received the case confirmation before you resigned, the case should be covered by ARAG.
  • HSA. The HSA belongs to you, your existing HSA card will be canceled, and you’ll receive a new HSA card (with a new number) a couple of weeks following your last day. However, you’ll now be on the hook for the 3.95/month administration fee and the 24/year investment fee. In my scenario, the instructions in the letter that arrived with my new HSA card were completely inaccurate. I had to call their customer service whereupon they redirected me to to create an account.
  • Microsoft Prime. 3 weeks later, my mobile membership to Microsoft Prime still works… 🤫
  • Last Paystub. You should receive your last paystub in the mail so it’s important that your address is up-to-date.
  • ESPP. If you were partaking in ESPP, and quit between a purchase period, you’ll receive a refund for the ESPP contributions you made in your last paycheck.
  • Vacation. In your last paycheck, you’ll be cashed out for all unused vacation days.
  • ❤️. Cherish the memories, and miss your old team dearly.

Good luck on your next adventure!