Rippling is a frustrating and disappointing suite of software for the staff-user to say the least. I've had 8 different issues with Rippling administering the HSA/FSA in the last 365 days.
1) Rippling allowed me to sign up for both HSA and FSA for 2020 open enrollment and then told me I was fresh out of luck and had to eat the $2k that was withheld for the HSA even though I was not in a high deductible plan. Until our HR admin and I fought them repeatedly for 2 months in early 2020 and finally got them to 'make an exception' from their error and give me my money back.
2) Throughout 2020 each time I submitted an invoice for reimbursement of Dr. visits when I didn't have my HSA credit card handy (about 6 times), they would reject the request for reimbursement EVERY time stating the documentation was blurry/invalid (even though it was a PDF invoice, system generated, not a screenshot or photo). The HR admin and I then had to push back on them and their support team each time, fighting to get my own money back that I was entitled to.
3) Now at the end of 2020 (12/26/20202) they showed in the Rippling portal I had the $2k of available balance and would lose the monies unless spent by end of 2020. So I went on a HSA-qualifying spending spree so I didn't lose the money. They then rejected those claims saying bugs in their system incorrectly showed I had a balance I did not. This has ended up being about a $1200 mistake. I asked them to reimburse me the money themselves at was a bug in their own system that caused the error, but they told me to pound sand.
Messing up a few times is normal, every software has bugs and mistakes, and people are human. But the repeated mistakes with real money on the line, to me demonstrates gross incompetence at best and fraud at worst.
Do better. Review collected by and hosted on G2.com.