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Tested on OpenBSD 6.2 and 6.3

Upgrade OpenBSD

Read the official FAQ.

Backup your data.

Download OpenBSD installer and verify its checksum:

# ftp $PKG_PATH/6.3/amd64/install63.fs
# ftp $PKG_PATH/6.3/amd64/SHA256.sig
# sha256 -C SHA256.sig install63.fs
(SHA256) install63.fs: OK

Plug in a USB drive:

# dmesg | grep removable | tail -n1
sd3 at scsibus5 targ 1 lun 0: <Vendor, Model, 1.11>
SCSI3 0/direct removable serial.12345678901234567890987654

In this case it appears as sd3.

Copy the installer image to the USB flash drive.

Be extremely cautious:

# dd if=install63.fs of=/dev/rsd3c bs=1m

Boot from that USB drive, then choose the (S)hell option to mount the encrypted drive.

# bioctl -c C -l /dev/sd0c softraid0
scsibus1 at softraid0: 1 targets
sd2 at scsibus2 targ 0 lun 0: <OPENBSD, SR RAID 1, 005>
SCSI2 0/direct fixed
sd2: 10244MB, 512 bytes/sec, 20980362 sec total
# exit

Choose the (U)pgrade option and follow the prompts similar to (install.html).

When OpenBSD upgrade is done, upgrade installed packages.

# pkg_add -u