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Tested on OpenBSD 6.4

Upgrade OpenBSD on Vultr

If you have OpenBSD installed on Vultr and want to upgrate it, then backup your data first.

Prepare

Login to your VM, download, and verify bsd.rd:

# ftp -V https://cdn.openbsd.org/pub/OpenBSD/6.4/amd64/bsd.rd
bsd.rd       100% |*******************************|  9782 KB    00:00
# ftp -V https://cdn.openbsd.org/pub/OpenBSD/6.4/amd64/SHA256.sig
SHA256.sig   100% |*******************************|  2141       00:00
# signify -C -p /etc/signify/openbsd-64-base.pub -x SHA256.sig bsd.rd
Signature Verified
bsd.rd: OK
# cp /bsd.rd /bsd.rd.63
# cp bsd.rd /
#

Read the official FAQ.

Update your configuration files, if needed for 6.4.

Access the console

Upgrade

Login via the console and boot from /bsd.rd.

OpenBSD/amd64 (xxx.xxx.xx) (tty00)

login: root
password: ********

OpenBSD 6.3 (GENERIC) #100: Sat Mar 24 14:17:45 MDT 2018
...
# reboot
...
boot> boot /bsd.rd

booting hd0a:/bsd.rd: 3511114+1500160+3892040+0+598016
...

Choose (U)pgrade:

Welcome to the OpenBSD/amd64 6.4 installation program.
(I)nstall, (U)pgrade, (A)utoinstall or (S)hell? u
...

Answer the questions:

Which disk is the root disk = sd0
Force checking of clean non-root filesystems = no
Location of sets = http
HTTP proxy URL = none
HTTP Server = cdn.openbsd.org
Server directory = pub/OpenBSD/6.4/amd64
Set name(s) = done
Location of sets = done

Wait for the installer and boot normally:

...
CONGRATULATIONS! Your OpenBSD upgrade has been successfully completed!
...
boot> boot /bsd
...

OpenBSD/amd64 (xx.xxx.xx) (tty00)

login:

Close the console.

Update packages

Login and update the installed packages:

# pkg_add -uv
...
#