Domain Transfer - Expiration Date Issue

I am planning on moving my domains to Cloudflare from Squarespace (thanks Google). I have one domain that just renewed with Squarespace on June 1, 2024. It’s expiration was June 17, 2024. Extended one year to 2025.

The transfer page in Cloudflare still shows the old expiration date and that when I transfer I will then pay for the one year extension, which it thinks is June 17, 2025. But I already paid for that and if paying again should push it out to 2026.

If I move forward with the transfer, will I pay again and still only get until 2025, or will the system get it right and actually extend to 2026?

Based on the information you have provided:

I will strongly advice against any transfers before July 17, 2024.

And, preferably, I would wait even longer, and NOT be doing anything before August 2, 2024.

Note: Both of these dates do however come without any guarantees.

What domain?

Cloudflare doesn’t set the rules for these kind of things, and as such, it isn’t technically Cloudflare, nor Cloudflare’s systems that are to blame.

Various rules can also vary a lot from TLD to TLD.

That said, and out of curiosity, … what is your definition of “get it right”?

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most gTLD’s (.com, .net etc) have a mandatory 1 year extension requirement when transferring. There is no way around that unfortunately. So, if your domain is a gTLD, cloudflare will automatically bill you for and add a 1 year extension to your domain.