Solved

As indicated by Jon Skeet above, the comparison was failing because of hidden millisecond differences in the times:

timestamp.strftime('%Y-%m-%d %H:%M:%S.%L') = "2014-08-02 10:23:17.000"started_at.strftime('%Y-%m-%d %H:%M:%S.%L') = "2014-08-02 10:23:17.679"

This discovery led me down a strange path to finally discover what was ultimately causing the issue. It was a combination of this issue occurring only during testing and from using MySQL as my database.

The issues was showing only in testing because within the test where this cropped up, I'm running some tests against a couple of associated models that contain the above fields. One model's instance must be saved to the database during the test -- the model that houses the timestamp value. The other model, however, was performing the processing and thus is self-referencing the instance of itself that was created in the test code.

This led to the second culprit, which is the fact I'm using MySQL as the database, which when storing datetime values, does not store millisecond information (unlike, say, PostgreSQL).

Invariably, what this means is that the timestamp variable that was being read after its ActiveRecord was retrieved from the MySQL database was effectively being rounded and shaved of the millisecond data, while the started_at variable was simply retained in memory during testing and thus the original milliseconds were still present.

My own (sub-par) solution is to essentially force both models (rather than just one) in my test to retrieve themselves from the database.

TLDR; If at all possible, use PostgreSQL if you can!

This seem to happen if you're comparing time generated in Ruby with time loaded from the database.

For example:

time = Time.zone.nowRecord.create!(mark: time)record = Record.last

In this case record.mark == time will fail because Ruby keeps time down to nanoseconds, while different databases have different precission.

In case of postgres DateTime type it'll be to miliseconds.

You can see that when you check that while record.mark.sec == time.msec - record.mark.nsec != time.nsec