Chatology Review: Flexibits Reinvents Messages.app Search

Chatology for Mac

Chatology for Mac

Chatology's main window. I only couldn't buy it because the Store wasn't available during the beta.

Flexibits, run by Michael Simmons and Kent Sutherland, makes two of my favorite apps. With Fantastical for Mac, released almost two years ago, they removed friction from event creation on OS X through a simple yet powerful menubar app that leveraged natural language processing. Fantastical is the only calendar interface that I interact with on my Mac, as it can send events to configured accounts directly – in the background – without needing Apple’s Calendar. Last November, they brought everything they had learned on the Mac to the iPhone with the release of Fantastical for iOS, a fantastic Calendar replacement with native iOS integration, a gorgeous Day Ticker interface, and advanced features such as a URL scheme and multiple alarms.

With the Fantastical brand, Flexibits has established itself as capable of building apps that use existing Apple technologies to create new, enjoyable experiences that are equally efficient, reliable, and rich in detail. Today, with the release of Chatology, Flexibits aims at supercharging a tough and infamous subject: Messages for Mac.

First released as a beta for OS X Lion users last year and then bundled into Mountain Lion as an app comprising the AIM and iMessage protocols, Messages has long been criticized for its technical flaws, instability, and poor performance with group threads and search. In my opinion, Messages for Mac gets several things right: for instance, iMessage is one of the few modern messaging services to offer a fully native Mac app, which is reflected in the way Messages supports features like Quick Look for inline attachments, Finder integration for drag & drop, or contact matching with the Contacts app. I have tried various messaging services in the past year, and – when it works – Apple’s iMessage through Messages for Mac is a pleasant, Mac-like experience. But that’s the problem: when it works.

For all the people who can attest their usage of Messages for Mac has never lead to issues or frustrations, there are thousands of users who, like me and my fellow MacStories teammates, have been struggling to cope with Messages’ problems and discrepancies over the past year. Just to name a few: the app often fails to send iMessages in spite of the iMessage service working from an iPhone or iPad; it displays messages out of order (e.g. a message from “yesterday” is displayed after a message from “today” in the chat window); it starts eating CPU resources and requires a force quit; it remains stuck on an old “view” of a group thread, requiring a force quit of the Messages.app and imagent processes; it beachballs whenever search is accidentally triggered in the main window, causing the app to go look for a text string in its log archive, which, for some, spans several months. And even after the OS X 10.8.4 update (which introduced a bug fix for messages displayed out of order), Messages.app still suffers from serious performance issues, especially when used extensively with group chats and search.

I like the idea of Messages for Mac, and I’m a fan of many of its parts. As I said above, other companies (like Google and Facebook) don’t believe in the necessity of providing a native Mac experience for its messaging services, whereas Apple has offered a native and integrated app from the get-go. Aside from matters of personal taste[1], the MacStories team and I found Messages’ unreliability and technical issues to be critical hinderances to our work-related communications, and so when Google came out with Hangouts, we immediately switched to it.

Flexibits knows that thay can’t change the Messages app, or make the iMessage service more reliable. But they have figured out a way to fix one specific aspect of the experience: search and retrieval of message content through logs. Chatology gives people who use Messages.app frequently the search tools Apple should have made.

Chatology works by scanning the chat logs Messages.app keeps in your system under /Library/Messages/Archive/ as folders organized by date. Since my fresh install of Mountain Lion last year, I have accumulated 5193 chat logs, which Chatology takes less than 15 seconds to scan and sort on my Mid–2011 MacBook Air. An option to save a history of conversations is available in Messages’ Preferences in the (aptly named) Messages tab.

Chatology for Mac

Chatology for Mac

Chatology displays three columns for the Messages conversations it finds on your Mac: on the left, a sidebar gives you access to individual chats, divided in “People” (conversations with individuals) and “Group Chats” (group threads); in the middle, conversations are sorted by date and time, showing how long each conversation lasted; and on the right, the actual conversation is displayed, with View options to show a log as “Balloons” or “Boxes”. Contacts are matched with the Mac’s Address Book, showing profile pictures (when available) and the phone number or email address used to start a conversation. Chatology’s design is clean and functional.

Flexibits’ unique spin on Messages log collection starts from how you can quickly launch Chatology directly from Apple’s Messages app.

Chatology for Mac

Chatology for Mac

Because Chatology is not available on the Mac App Store, Flexibits could sidestep Apple’s limitations and create an option to override Messages’ default ⌘F search shortcut to activate Chatology instead. One of Messages’ most common annoyances is, in fact, how accidentally triggering a search (either by typing in the search field or hitting the keyboard shortcut) can cause the app to halt and become unbearably slow. With Chatology’s keyboard shortcut override, you can hit ⌘F and be taken immediately to Chatology, where you can start typing right away.

Searching in Chatology can be done in two ways: you can look for messages that contain a specific text string, or recipient names that match your query.

Chatology for Mac

Chatology for Mac

Results are organized by chat, highlighted in the conversations column, sorted by date, and you can click them to be taken to the part of a message that you were looking for. Alas, results aren’t highlighted by default in the main log panel, but you can press ⌘G to highlight and navigate between them.[2] I would like to see support for more Finder-like tokens in search: “chat contains” and “name contains” are useful, but I would love to be able to combine multiple text, name, and date tokens for an even more precise search scope. In my tests, searching with Chatology was fast and reliable, with results highlighted almost in real-time as I was typing in the search field.

The lack of customizable search tokens is compensated by Chatology’s date and content filters, which I found to be solid additions to regular message search. In a top bar that runs across the main toolbar, Chatology displays five date filters to restrict search (and browsing) to All, Today, Last 7 Days, Last 30 Days, and Last Year; I would like to be able to have my own date ranges in there, but I understand why Flexibits went with these five default options in the first version of the app. Either when searching or simply browsing around Chatology’s logs, you can click the date filters to have the app change the scope of matched logs and see the results reflected in the sidebar and conversations in the middle. In my experience, however, I found Chatology’s three content views to be the most powerful tools in my workflow.

Chatology for Mac

Chatology for Mac

In the conversation view, you can switch between a general view (showing a conversation as it appeared in Messages) to image-only or links-only views. Having used Messages as the primary communication tool with my team for several months, you can imagine the amount of memes, screenshots, and URLs we’ve shared; with Messages, there’s no easy way to retrieve those individual items, unless you’re willing to fire up the Finder’s folder-based archive and look through hundreds of chat views for all messages sent within a group chat. Chatology fixes this problem by looking into the logs, analyzing their contents, and enabling you to open a view of images or URLs alongside the date and name of the person who shared them. And yes – animated GIFs are displayed inline.

Chatology for Mac

Chatology for Mac

I’m a big fan of this feature, and if you’ve been using Messages extensively to share images and web links, I believe this alone will make Chatology worth your purchase. For our team, it used to be that screenshots and silly in-jokes would be forever lost in a myriad of Finder files nobody wanted to go through; with Chatology, I have found old photos and references that I knew were there – somewhere – but that Apple’s Messages app couldn’t easily bring up. Chatology does this job in an excellent way – with a simple interface that doesn’t require me to fire up the Terminal and start looking for files manually inside a conversation, or, worse, take forever to load “earlier messages”. More importantly, Chatology provides visual context for the attachments it finds, allowing you jump back into the place in a conversation where an image or link was shared, letting you understand who shared what, when, and why.[3]

Aside from the minor additions I have mentioned so far, there are other features that I’d like to see in a future update to Chatology. In my log archive, some group threads belonging to the same day are split by Chatology into multiple entries; I don’t know if this issue may be related to all those times we needed to restart Messages group threads from scratch (it happened several times), but I think Flexibits should figure out a way to group those under a single day. I also noticed that, in a few group chats, some images would show up as “deleted”, GIFs would be repeated multiple times, and sound attachments would appear as “deleted” as well. These were sporadic issues that only took place with 2–3 conversations I had found with Chatology, and I wouldn’t be surprised to know the bug was actually caused by Apple’s Messages app. Overall, Chatology performed admirably with over 5,000 logs in my archive.

In terms of features, it would be interesting to explore the idea of visualizing Messages stats in Chatology. I’m intrigued by the possibility of viewing which ones are the top domains shared with URLs, or the times of the day when I’ve been most active, and with whom. In the sidebar, I’d like to see my contacts grouped in the same way they’re organized in groups in the Contacts app, though I don’t know how that would scale for group chats. Speaking of group chats, mine are displayed in the “Chat with [User Name] et al.” format, which I understand is also how Apple archives them in the Finder, but that, considering how Chatology can look at the email addresses and phone numbers of the participants, I would like to see as a full list of names rather than “et al.” in the sidebar. When browsing, I wish Chatology could save me clicks between days and consolidate conversations into weeks and months. And last, I would obviously welcome a GIF-specific search token as well.

Last week, Apple didn’t announce any major new Messages-related feature, although the company could obviously overhaul the app before OS X Mavericks hits the shelves later this year. Today, Chatology is a fantastic addition to Mountain Lion’s Messages app: it shows how third-party developers can still take advantage of the Mac’s nature to build solutions that fix and improve upon Apple’s built-in apps. I encountered minor issues in the final version of Chatology that I was provided by Flexibits; as I outlined above, I find great utility and potential in Chatology, and I can’t wait to see if and how its developers will expand upon the current feature set.

Flexibits found the perfect niche for Chatology, one that Apple ignored for too long and that I’m now enjoying on a personal level every day. Since I started using Chatology, I have re-discovered photos of my trip to the Amalfi Coast that I sent to my parents last summer, or memes and funny jokes that I shared with the MacStories team – alongside the more serious stuff – several months ago during Apple keynotes and regular work days. I wish Flexibits could make Chatology for iOS, but, alas, they can’t.

If you use Messages for Mac on a daily basis and always wanted better search and archive browsing features, Chatology is, in my opinion, a must-have. There’s a free trial, and you can buy the full version for $19.99 from Flexibits’ store.


  1. Some users don’t like the fact that Messages combines iMessage and AIM into a single application. I don’t mind Messages’ unification of chatting tools, but I’m not a heavy AIM user in my daily workflow. I do believe that Apple could use some clarity in the way AIM and iMessage threads are displayed in the app’s sidebar, but I don’t use AIM enough to be able to provide a meaningful suggestion about it. I certainly won’t be making a mockup to post on Dribbble.  ↩
  2. Other options are available under Edit > Find, such as a Mail-like “Use Selection for Find” item.  ↩
  3. Chatology also lets you open a log in the Finder, or export it as plain text.  ↩