OpenBSD Upgrade Guide: 6.5 to 6.6

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Upgrades are only supported from one release to the release immediately following it. Read through and understand this process before attempting it. For critical or physically remote machines, test it on an identical, local system first.
Start by performing the pre-upgrade steps. Next, boot from the install kernel, bsd.rd: use bootable install media, or place the 6.6 version of bsd.rd in the root of your filesystem and instruct the boot loader to boot this kernel. Once this kernel is booted, choose the (U)pgrade option and follow the prompts.

Alternatively, a new unattended upgrade method has been introduced. The sysupgrade(8) program is available as a syspatch(8) for OpenBSD 6.5 on the i386, amd64, and arm64 platforms. Once installed, the upgrade can be performed by running sysupgrade.

Another option is using the manual upgrade process (although this is not recommended).

After upgrading the sets, apply the configuration changes and remove the old files. Finish up by upgrading the packages: pkg_add -u.

You may wish to check the errata page for any post-release fixes.

Before rebooting into the install kernel

Configuration and syntax changes

Files to remove

Special packages

Upgrade without the install kernel

This is NOT the recommended process. Use the install kernel method if at all possible!

Sometimes, you need to do an upgrade of a machine for which the normal upgrade process is not possible. The most common case is a machine in a remote location and there is no easy access to the system console.


Upgrading manually

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