There is an issue introduced with a recent OpenSSL 1.0.2k update where a pkgin upgrade will render the pkg_install tools (which includes pkgin) unusable, due to removing the previous openssl package prior to installing the update.
Here is an example error message you would see when attempting to use pkgin:
# pkgin update
ld.so.1: pkgin: fatal: libcrypto.so.1.0.0: open failed: No such file or directory
If you wish to upgrade your 16.4.0 image (via pkgin upgrade) you need to first update the openssl packgage using the pkg_add command:
pkg_add -U openssl
This will upgrade the openssl package in place and then the remaining upgrades can be handled normally via pkgin.
If you have already broken a system with pkgin upgrade you can fix the pkg_install tools (and pkgin) by doing the following:
New naming scheme and introduction of Long Term Support (LTS) releases:
All image names now include the architecture information. For example minimal-32 for 32-bit, minimal-64 for 64-bit and minimal-multiarch for multiarch.
All fourth quarter (Q4) pkgsrc releases are now LTS releases. Packages in an LTS release will receive security or build fixes for 3 years from the time the release is made available (assuming the fixes do not affect API or ABI compatibility)
Images based on a pkgsrc LTS release will have a new -lts suffix added to the image name e.g., minimal-32-lts
14.4.0 represents the first LTS pkgsrc release
SmartOS packages are now PGP signed and verified during install.
The 14.4.0 images (and pkgsrc 2014Q4 packages) require a minimum platform of 20141030T081701Z