I've had this problem for a long time (over many OpenBSD releases). The pkg_add man page (for 4.5) states:
"If a given package name cannot be found, the directories named by PKG_PATH are searched. It should contain a series of entries separated by colons. Each entry consists of a directory name. URL schemes such as FTP, HTTP, HTTPS, or SCP are also appropriate." On a client machine: PKG_PATH=http://$HTTP_MASTER/:http://$HTTP_MASTER/by_port/i386/all/ My master server serves up normal packages and those packages compiled from ports. When I do this only the first component is searched. I have to do a second package update run with PKG_PATH pointing directly to the second component for the "ports packages" to be seen. Why is this? -- /jm
