To really see what's going on, right-click on the "similar" emails and do View Original. Then compare the spam scoring in their mail headers. You should see progress in the sense of the Bayesian scoring getting higher over time.
However Bayesian scoring alone isn't enough to auto-recognize junk on a stock Zimbra system. The reason: on a stock system, Bayesian only scores up to 3.5, and the spam threshold is 6.6. So look again at those headers and see what the total score is. If at least 3.1 "points" come from scoring other than Bayesian, then Bayesian will eventually suffice. Otherwise you should consider tweaking the spam settings.
The easiest thing to do is just to lower the threshold via the Admin GUI (I believe it's under Global settings). For more advanced tweaks you should search the forum and the wiki.
One thing to watch out for, though, is
Bug 31333 – Emails from authenticated users getting marked as spam Bug 12277 – Add support for better antispam scoring of sasl authenticated senders
The upshot of these is that if you set the threshold too low, then mail from legitimate users may be marked as spam simply because they're connecting from external networks. See comment #10 in bug 12277 for the necessary customization.