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For everything from applicant tracking systems to databases, I often think "at least it isn't an Oracle product." Seems like some other company could use this given enough of us already think it.

I know this will be down-voted for being a Reddit-esque comment, but it was worth it.

"90s database technology" in the sense that it's hard to work with and the support costs are unnecessarily high. The protocol is hard to work with - which makes debugging less appealing and thus most people avoid trying - and no server I've seen with the arguable exception ActiveDirectory has well-designed logging for typical sysadmin needs.

Beyond that everyone other than Microsoft uses the OpenLDAP code, which has a number of basic errors and rough-edges. slapd has numerous deadlock conditions and the only backend which doesn't have a low risk of corrupting your data (MySQL) is discouraged. The client libraries had basic design failures for aeons - the most glaring being the assumption that the network is perfect and will never drop or delay packets (timeouts are checked after blocking operations return, which takes several days due to retries at multiple levels). This means that OS X, Linux, FreeBSD, etc. clients will become unusable if your LDAP server is less than perfect - and since slapd deadlocks under normal use, this will occur sporadically. The developers were largely in denial about this - my patch to set SO_RCVTIMEO / SO_SNDTIMEO was ignored with unproven claims that this would magically work in the bleeding-edge trunk version (untrue then, could have changed now) but the libpam-ldap maintain is more conscientious so the similar patch there was accepted a couple years ago so at least Linux clients actually attempt to failover.

Honestly, whether you call it 90s database technology or 90s directory technology doesn't really change the fact that it's a pain to work with.

I read the Engine Yard story before, and it's a really good evaluation of where things went wrong for LDAP.