Boxer vs Outlook for iOS: The Match of the Century

Boxer vs Outlook for iOS: The Match of the Century



Over the last year or so, I have been going back and forth on what the best mail app is on iOS. For awhile it was Boxer because of terrifying security risks with the Outlook App and then back to Outlook after Boxer decided to stop working properly with notifications. Thanks to the product team for Boxer, I have decided to take some time to re-evaluate this once more. My review is completely unbiased and looks directly at the facts. Far too many people have a dog in the fight, whereas I just focus on the truth.

We will evaluate the clients in a few categories:

  • Email
  • Calendar
  • Contacts
  • Content Management
  • DLP


We measure email with a few key measurables that you will see in the table below.

FeatureBoxerOutlookThe Winner
Email Sync 
Outlook has a slight edge. They sync a copy of the mailbox to Azure. This lets you work with attachments without downloading them and searching quicker. Boxer does offer one very nice unique feature, where you can sync and get notifications on sub-folders which as a former BlackBerry diehard love!
Quick Actions
Boxer has an edge here. They offer many more actions (create tasks from email, quick message, spam. They also support twice the swipe actions (short and long for Boxer). Boxer is also much more intuitive for selecting messages and using actions.

Outlook does offer one very cool feature to postpone a message to return to your inbox at a later time.

Convo View
Boxer’s current BETA has a brand new conversation view that is a MAJOR step up and completely beats Outlook. You can also configure the conversation order and whether unread messages are automatically expanded.

Outlook’s conversation view is so confusing and painful. Boxer has really cleaned it up and moved attachments to the top of the message to win this category.

Email Notifications
Oh AirWatch, you try so hard to fix your notification service but its just not there yet. I’ve discussed it in other blogs so I won’t spend time there.

Outlook wins this by a lot right now. Notifications work quite well in Outlook as long as you are regularly opening the mail client. Once ENSv2 is clean, I think these two can meet pretty close in the middle but its the biggest hurdle on the Boxer client today.

Email Search
As mentioned earlier, the Outlook service in Azure’s caching service does wonders. It makes email search so much faster than ActiveSync allows for. Boxer’s search is good, but Outlook is just better.

Winner: Outlook wins this by a narrow margin. If notifications were a bit more solid, Outlook would lose easily. The user experience in Boxer’s inbox is SUBSTANTIALLY stronger than Outlook. I know many people love the Focused Inbox, but I am not one of them. It takes a lot of work for a normal person to manage and configure the Focused Inbox. In my opinion, it should have some AI built inside of it to adapt and adjust. Outlook’s bread and butter are attachment processing, email search, and notifications all key staples of the Outlook Service which I detail here


Calendar is the most painful technology for mobile productivity. It’s usually inaccurate and a big epic fail. Let’s get to the head-to-head!

FeatureBoxerOutlookThe Winner
Calendar Sync 
Boxer gets a slight edge here for a debatable feature. You can pull in personal calendars from outside Boxer as “visible calendars” to create a unified calendar.

Sync on both Outlook and Boxer are very solid outside of that niche feature.

Calendar UI
Boxer has a solid edge here. They both offer Daily/Agenda views, but Boxer takes it a step further. You can see when days have multiple meetings with a dot system without going into them. They also offer dropdowns to change months and provide a better flow to navigate to different days/times/months. Boxer also has a neat little feature where it captures any phone numbers in the invite and provides them as a clickable field to easily dial into a meeting.
Free/Busy Lookup
Boxer’s new BETA introduces this amazing new ability to free/busy lookup attendees for creating new calendar items. For the first time, I actually feel comfortable creating calendar items on a mobile device. That is such a HUGE deal as since iOS 7 it has been a major headache.

Outlook has introduced this, but the UI around this is a nightmare. Most people expect that when you create a calendar item from your mailbox that it will use that calendar. This is not the case at all!

Calendar Attendee Features
Outlook wins this one with the only differentiator for Boxer is that it will do automatic GAL lookups against your directory. The best thing that Outlook does here is when you drill into a Contact it shows you related emails and files.

It’s nice that both give you the ability to email attendees and forward calendar invites.

Winner: Boxer edges this one out.  Outlook really only gives you the history feature, but the fact it gives you a limited amount of emails and is not very intuitive is a definite gap that I see. It has a ton of potential though overall. Originally I missed how they implement free/busy in the calendar in Outlook. If someone with my experience misses this if you have multiple mailboxes then your users definitely will too. Basically, if your Exchange mailbox isn’t the default calendar it will be very cumbersome. The Boxer team has clearly spent significant time in developing the calendar into something would want to use.


Winner: I’m not going to be using a table or anything fancy for this section. Outlook’s contact view is much better. They don’t have a dedicated contacts tab, but it’s more of a unified search capability within Outlook that I prefer. Any contact you access, you get all sorts of great information including messages and files involving that person. It’s the true spirit of enterprise search. This is a feature that Boxer needs to adopt as its brilliant.

Content Management

Winner: Outlook wins this one by default. VMWare is working on building in OneDrive integration into their application, which we expect to see later this year. Once that gap is closed then this is a moot point. From a security perspective, I hate that Outlook supports personal cloud providers and you cannot block them, but oh well!

Microsoft does one thing very well in every product and that is bring them all together. Accessing files in OneDrive via Outlook is so clean and crisp that it is the gold standard in enterprise content management within a mobile application. Boxer’s design has always been to leverage secure open in. It’s hard to criticize that idea since its the entire spirit of mobility DLP (yay Secure Open-In). Boxer does allow you to use the Apple Files app, but unfortunately when you enforce Secure Open-In you cannot access your OneDrive in the Files app. I eagerly look forward to seeing OneDrive seamlessly into Boxer.


The DLP can be a bit confusing so I thought it would be good to clarify it. We will detail the feature available in both and provide a bit of insight.

FeatureBoxerOutlookThe Winner
DLP Features 
Boxer has a clear advantage in its DLP capabilities over Outlook. Boxer lets you restrict (Copy/Paste, Sharing of Email/Attachments, Personal Accounts, Contacts, Printing, Restricting attaching files from personal cloud vendors, and the ability to classify emails). Additionally, you leverage the capabilities of Secure Open In for a MDM-managed device to control what apps you can open Boxer content into (e.g. Content Locker, OneDrive, etc)

Outlook lets you restrict (Copy/Paste, Sharing to non-Microsoft Apps). They also have some capabilities that are general in nature for “prevent save as” which does appear to only block a few cloud providers but does not eliminate all cloud DLP risks. That is more of the responsibility of IRM in an Exchange Online world.

Winner: Boxer is clearly superior on DLP. You can properly close the gaps on both, but there are clearly more complicated ways of closing some of the gaps depending on your preference. I do prefer a design of using the AirWatch Secure Email Gateway with VMWare Boxer to have a stronger/more secure client. I do think both are very effective in DLP, but the concern is that Outlook’s policy are general and not geared toward Outlook.

Miscellaneous Features

One final thing to cover regarding these products are the add-ins. In the Office 365 world, people will be adding mobile support for their add-ins which you can deploy via Office 365/Exchange Online. This will require either a good developer or two on your team to custom build/maintain your add-ins or some financial considerations to further these capabilities. I think these will be a big part of the future of DLP. We really need to extend more of the functionality we achieve on Outlook at the mobile level.

VMWare does this a bit different with Mobile Flows which are basically little javascript apps that run server side and integrate with the mobile SDK to let people do some really dynamic things like approve JIRA tasks inside of Boxer or approve a WorkDay expense. The reason I highlight these some much is that in the near future we will get access to some OOTB (Out of the Box) mobile flows that won’t require a developer. Of course, you can get access to some stronger mobile flows if you build your own app similar to Outlook, but the sheer ability to achieve some dynamic digital transformation at your organization for minimal technical effort is the spirit of digital transformation (I hate that C-level buzz word but it actually applies for once!)

In Conclusion

So we went through the key components of two very good mail clients. Everyone has their own opinions and many of those are clouded by a few key things:

  • Pressure from management to get rid of AirWatch and go to Intune
  • Blind loyalty to AirWatch or Microsoft
  • Looking for simplicity and not needing to manage infrastructure

My views and opinions here are completely objective as a former support engineer at BlackBerry (the company that pioneered the gold standard of PIM) and who has used almost every mail client and mobile platform that exists. So I will say it very simply and broadly. I think Outlook and Boxer are about even right now. 6 months ago, I felt Outlook was crushing Boxer, but they have been receptive to feedback and have addressed many of the concerns their customers have provided.

The only reason that Outlook “could” be seen as superior to Boxer right now is the substantial failures of the email notification service. It has its good days and bad days obviously, but consistency is the most important thing for any piece of technology. I think if you can work through the notification issues, then Boxer could be growing into an amazing product. I’ve transitioned from being optimistic about ENS to conceding its not very good at this point and hoping they surprise me.

Update: I would say that they are much closer today than I thought originally. I have been able to fix ENS v1 to a workable state using Push Notifications over the last few weeks and Outlook does offer Free/Busy despite me being sucky at my job when I reviewed these a few weeks ago. The major gap that exists here at this juncture for those of you that leverage OneDrive for business is the ability to directly attach files from OneDrive into Boxer. I have found a “crappy” way of doing it, but they are going to enhance that in a few months. I will be updating my DLP blog post to reflect that.



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