September 5, 2026 · 4 min read
Pink Jeepney vs Hightail
Hightail keeps a file close. Pink Jeepney is trying to let it leave.
David KrugManila · @realDavidKrug
The upload is the easy part. Everyone can build an upload. The product is what the file does after that.
Hightail used to be YouSendIt. It grew sideways into creative review: comments on the work, not just a download.
What Hightail is actually for
Review in the same place as delivery is genuinely useful for a studio that lives in rounds.
If the file only needed one trip, a home for it is a strange gift.
The free send is modest and easy to outgrow. This is not the tool you open for a one-off ZIP.
You pay for a workspace where a client can mark up a cut or a layout.
Where it gets awkward
If you only needed the file to arrive, you bought a conference room to mail a letter.
The numbers, side by side
| Pink Jeepney | Hightail | |
|---|---|---|
| Free size | 2 GB | Modest |
| Free expiry | 7 days | Short |
| Account to send | No | Yes, for the real product |
| Password | Paid plans | Paid |
| The top end | 250 GB on Business | A review room, not a bigger truck |
Read the row you care about and ignore the rest. Most people only have one complaint. Size, or time, or the account.
What I would do
I would stay with Hightail if the feedback on the work matters as much as the file.
I would use Pink Jeepney when I want a delivery with a checkout: one link, a sentence on the ticket, a zip if I sent a pile, and a burn switch if one download should be the end. Free is 2 GB for 7 days, three times a month. Past that the plans are $9, $24, and $59.
If you will still want the file in their account next year, you wanted a drive. If you wanted it gone after they took it, you wanted a transfer.
Written by
David Krug
Twenty-plus years of building cute little websites, and big ones, with an independent footprint. In the Philippines since 2016. Based in Manila, with two children and one amazing partner.
Follow the build · @realDavidKrug
