How to Lose a Customer After 15 Years: A Dropbox Case Study

(Or: Death by a Broken Upgrade Button)

For the last 15 years, I’ve paid for

Dropbox

. Happily.

Through startups, moves, acquisitions, and side projects, it’s been the one constant in my digital life. I’ve referred friends and evangelized the brand. I’ve been what most #SaaS companies would call a dream customer.

Until I tried to upgrade.

🚧 A Simple Request, Ignored

In July 2025, I reached out to @DropboxSupport with a straightforward ask:

• Migrate my legacy account to our startup domain: @kimono_inc
• Retain the 15TB+ of data I’ve already been paying for
• Add #DocSend and #DropboxSign (which I wanted)
• Apply one of several #startup discounts we qualify for via #StripeAtlas, #MercuryBank, and #Brex
• Bundle everything under one unified #DropboxBusiness contract with predictable billing

I even drafted a comprehensive onboarding document — the kind that most enterprise sales reps would kill for.

What happened next was… not that.

🤯 The Support Loop from Hell