Review: Hard as it tries, Chatology can't overcome Messages flakiness

iChat’s transformation into Messages was not exactly welcomed with open arms by Mac users everywhere. Some find the integration between iMessages and instant messages clunky; others have experienced a lot of flakiness (some of which Apple claims to have fixed in a recent OS X update); and yet more don’t like the app’s search functionality.

It’s the last of these that Fantastical maker Flexibits has focused on with its newest app, Chatology. The software aims to revitalize the Messages search feature, providing advanced functionality that makes it even easier to find the messages that you’re looking for.

Though it’s a standalone app, Chatology does integrate with Messages; when you install it, the app hijacks Messages’s Command-F shortcut. Use that key combination and Chatology launches automatically. (If you’d rather it only launch manually, you can deactivate that feature in Chatology’s preferences—in fact, it’s the only option there.)

Searching in Chatology is much like searching in messages. Enter a search term in the field in the top right of the window, and you’ll be presented with a list of results that match. When you enter the search term, the app also lets you choose to search for conversations that contain that term or places where that term appears as a name—for example, I can search for chats about my friend Evan or chats from my friend Evan.

One major difference between Messages and Chatology’s respective search features: While the former will find a string even if its inside a word (for example, searching for “in” will return results with the word “think” and anything else that contains “in”), Chatology searches for the term as a whole word. The latter usually, though not always, provides better results.

Chatology’s major attempt to improve on Messages’s searching is its ability to filter search results. A bar on the top of the window lets you choose from certain time windows, including all messages, only messages sent today, those sent in the last 30 days, or those sent in the last year. While those are quick and handy filters, it would be nice if Chatology also let you specify a more abstract range.

The leftmost pane breaks down your conversations by people (group chats are broken into a separate section). Select a person and you’ll see a list of dates when you conversed with them. One downside here is that Chatology doesn’t do as good a job as Messages does of grouping the same contact; if you converse with someone both via their phone number and their email address, they’ll appear as two separate contacts.

In the rightmost pane, you can choose to filter by three types of data: conversation (text), images, and links. Select any of them and you’ll see only that type of information, letting you quickly browse images or links in that conversations. Images are shown inline—you can even Quick Look them by using the button in the toolbar or by selecting them and hitting the spacebar. In the case of both links and images, you can click an arrow icon to be taken to their location in the conversation at large.

While all of that can be helpful, I found myself wishing for more. For example, sifting through search results can be a pain: As in Messages, you still need to click on each individual person to see the responses; Chatology adds an extra layer by then requiring you to select each conversation in turn. If you filter by images or links, you’ll often end up with multiple conversations that don’t have those types; instead, Chatology will report “There are no images in this conversation.” I’d rather instead that conversations that don’t match simply not be shown. In a concession to that, at least Chatology does display the number of images or links in a conversation next to the respective filtering option.

Making the experience more problematic is the fact that Messages’s logs are a bit of a mess. You can view them in the Finder at ~/Library/Messages/Archive; in many cases, you’ll see duplicates of the same conversation, or excerpts of a larger part of the conversation. And because Chatology pulls from these archives to provide search results, it too will often show multiple results for the same conversation. For example, a conversation with one of my cousins on December 20, 2012 showed two entries, both for 5:15 p.m.—one lasted 29 minutes, while another lasted just one minute. Some cases were more extreme: In one case, there were two entries, one lasting 1 minutes while another lasted 2 weeks.

In the case of group messages, I often encountered the same issue, as well as sometimes seeing only part of a conversation. (The latter issue seemed to be resolved thanks to a tip from the developer: Holding down the option key and selecting the File menu displays a hidden option to Rebuild Log Cache.) And Chatology only displays the name of one of the group chat participants, which can be misleading: For example, clicking on a group chat listed as “Chat with Chris Breen et al” yielded only a single message from my colleague Lex Friedman. However, I couldn’t seem to locate that conversation at all in Messages, so Chatology at least earns a point there.

I also ran into a problem with Chatology’s delete feature. You’re supposed to be able to remove conversation logs by selecting them and clicking the Delete button in the toolbar. When I did so, I was asked to confirm that the selected log would be moved to the Trash—but even when I did, the conversation stayed where it was. Upon further investigation (Chatology helpfully lets you view a log in the Finder, either by using a toolbar button or control-clicking on a conversation and choosing Show in Finder), I found that there were several duplicates of the same conversation, and each time I chose delete, one of them was removed.

Bottom line

Overall, Chatology might be an improvement on Messages searching, depending on your level of frustration with the current functionality, and how much you use Messages. While many of the issues I experienced with Chatology can be laid at the feet of Messages itself, that doesn’t unfortunately make the experience any better. As I understand it, the work required to make Chatology correctly address the duplicate issue would not be insignificant, but as this is a utility whose sole purpose is to improve upon Messages search, it seems to me that that would be a worthwhile investment.

Flexibits is offering a 14-day trial from its own site if you want to give it a shot before buying. (The app isn’t available in the Mac App Store.) While it may entice Messages power users, its $20 price tag is probably a bit high for casual Messages users.

Updated on 6/19 at 6:14 a.m. PT. An earlier version of the review said that Chatology doesn’t highlight terms in conversations when you search for them, which is not the case.