Those who frequent my blog are familiar with my multiple articles over the years comparing Boxer and Outlook. First, we will cover a bit of history. I was working in the DoD many years ago and I was struggling with s/MIME because Apple doesn’t check certificate revocation. The only solution that could meet these needs was the AirWatch Inbox. Yes this thing!

As my travels over the years would stop at several different industries and organizations, Boxer has followed me. It hasn’t always been easy as the Boxer acquisition has been challenging. Today, things have improved with various enhancements like FastSync, which I wrote about here. We will discuss the different aspects to an email client and discuss which one has the edge. I don’t pull any punches and I stick to the facts. Let’s get started!

ActiveSync Capabilities for Boxer and Outlook

Email

Email is the reason we are here. We use these apps to deliver email to mobile devices to empower the digital workspace as much as I hate that jargon. Both Boxer and Outlook offer different “nice things” but both have some gaps.

Boxer’s Email Capabilities

Boxer supports email fairly well today. One of their interesting features is “Custom Mailboxes” which lets you create a mailbox that will appear in your Mailbox side panel and can encompass multiple Exchange folders. It’s a nice experience and supports background synchronization of items, which is very useful.

Another feature that I am fond of are the quick templates. The basic idea is you create a list of common replies or emails that you send and can send them in a single-click. We will cover that more in the user experience section, but they are very useful. I do wish you could build these in Workspace ONE (WS1) and deploy them, but I find them to be very useful.

Boxer also supports delegated access e.g. adding shared mailboxes or accounts you have permissions for. This is certainly useful for people in IT who own mailboxes or administrators.

The last item that we want to cover when it comes to email are notifications and FastSync which I won’t cover in detail. You can read my article from last year on ENSv2 for a better understanding. Simply, there is a service called the Email Notification Service, which will deliver real-time notifications to your devices using Exchange subscriptions. We now couple this with FastSync that provides a major difference maker: it syncs your email when your device is locked, which Outlook cannot do.

A few other things that Boxer supports, which I like are:

• Controlling whether you do Plain Text or HTML synchronization of emails
• Refetching empty links using MIME, which helps for non-standard URL schemes like the schemes that open you into apps like RSA.
• Controlling attachment downloads

The main issue that we have with email on Boxer is that it is not a great experience with Office 365. Many of the capabilities that people love in Office 365 are unavailable, such as Groups and the Focused Inbox.

Outlook’s Email Capabilities

Outlook’s email excels in its simplicity. The view is clean and concise similar to the desktop client, which is a huge asset. One of the issues that I have with Boxer is that there is no filter button. Of course, you can search and use the “All”, “From”, To”, and “Subject” buttons, but that isn’t how people use Outlook. I’ll cover this a bit more in user experience.

For Office 365 users, the additional APIs in the Outlook application are huge! You get the Focused inbox and Groups access that you know and love. That really matters and you can’t spin that.

Honestly, beyond that there isn’t much more to the email support for Outlook. Outlook doesn’t blow you away by any means, but they know how to do their job very well.

Calendar

Boxer vs Outlook’s Calendar Capabilities

We can cover this in one section because there are few differences. Boxer basically has a few standout features, which are just better. It has the following:

• Supports a default event length setting when creating new invites
• Supports supports synchronizing local calendars. This is a HUGE deal. I had a CIO who would NOT use Outlook just because he couldn’t access his iOS Family calendar.

Outlook does have a few that stand out:

• Separate reminder settings for All Day meetings vs regular meetings

One other thing that Outlook does extremely well that merits some visual queues is user availability. Boxer does not do a great job of this despite some improvements.

Outlook will show you who is unavailable with just a tap of a single button.

You can simply see by the avatars who cannot make the meeting. Honestly, I wish they would both implement suggested times similar to Outlook on desktops, but Microsoft does a nice job here.

Contacts

Contacts in general is a MAJOR fail by Microsoft and to a lesser extent with Boxer. They took the short way out on Contacts and it really frustrates me as a technologist. Simply, Microsoft and VMware copy your Exchange/O365 contacts to iCloud for Caller ID. The ways this is unacceptable are substantial. They essentially create a major fiasco for DLP just to let Caller ID work for users.

Luckily you can block that functionality either via Microsoft’s App Protection Policies or Boxer configuration settings. One area that VMware does a nice job here is they expose local contacts to the Boxer application, which is a nice feature for users, which we will discuss more of next.

Recapping ActiveSync Capabilities

As we discussed above, both platforms have varying skill sets. As it stands currently, Outlook is a superior email client for Office 365 mainly based on their secret sauce. Boxer is a huge step up for Exchange On-Premise users when built correctly and leveraging the right infrastructure e.g. ENSv2 and FastSync.

It does boggle the mind why they haven’t implemented the Graph API, which is available as seen here. I know it’s not a small effort, but the reality is in Office 365 you need certain things. The user experience and integrations we will discuss next are difference-makers to users.

User Experience

User Experience is always an interesting concept, which we will discuss a bit more in depth. We will talk about what VMware and Microsoft are doing to deliver a strong user experience.

Boxer’s User Experience

Boxer’s user experience is designed with an ergonomic mindset not dissimilar to BlackBerry’s concepts around BlackBerry 10 when that first came out. When we talk about user experience, it’s about usability that requires no explanation. The application must operate like your mind does. They do a nice job with email from that perspective.

Boxer’s Email User Experience

When composing emails, you can send Quick Actions, like we mentioned earlier or send times you are available. It’s very useful and Microsoft has emulated it more recently, but it’s truly working like you think as a person. You can even create meeting invites from the email compose view, which is by far the best way to do it with Boxer.

On a similar vein, one of the issues I run into frequently which is a big inconsistency is when creating meeting invites from the calendar pane. If you tap, ANYWHERE outside of the box that pops up it closes without a saved draft or ANYTHING.

Swipe Actions

Another item that I love to highlight when thinking about user experience are swipe actions. Boxer supports twice the swipe actions that Microsoft does. They have short swipe and long swipe actions for a total of 4 items.

You can configure several different possibilities: Actions, Archive, Delete, Move, Flag, Phishing, Quick, Read/Unread, Spam, and To-Do. One issue that I do have, which I sent over to product management is they don’t support phishing as an action you can deploy.

Additional Boxer User Experience Features

A few of the other things that I love with Boxer from a user experience perspective are:

• Local Calendar and Contact Accessibility
• Custom URL Schemes
• Real-time notifications and background sync
• Sending Logs automatically composes an email with your help desk email address, which you configure
• Ability to deploy customizations for the user experience like:
  • Swipe Actions
  • Skipping the Setup Wizard
• Siri Shortcuts (wish you could enable these via MDM)
• All opened attachments are stored in the Files Tab to email or share out.

Outlook’s User Experience

As I have mentioned in previous sections, Outlook does a great job catering to their users. The main tenet of user experience that I will always talk about is “same experience on every device” and Microsoft crushes it.

Outlook’s Email User Experience

The UI is clean and simple, which looks so similar to the desktop client. It’s exactly what you would expect. You have your focused inbox, filter button, trash, and a command list with our friend the 3 dots.

The compose view is VERY similar to Boxer as they have clearly copied a few of Boxer’s great ideas. I can’t really blame them can you? One very neat thing is the ability to create links inside of emails, which is just brilliant. They really get the idea of delivering the same experience across a myriad of options. Another item that I love as of late is the ability to read your emails to you, which as we know is a great user experience. Accessibility is just a cousin of user experience people! They are preaching my gospel!

Additional Outlook User Experience Thoughts

A few other items about Outlook’s user experience that I really enjoy are:

• One-touch buttons tied to meeting application URL Schemes like Zoom

• Very strong integration options (which we will cover in the next section)

Outlook Contact Insights

I don’t know if they call it insights, but that’s how I refer to it. Basically, you search for a user inside of Outlook and it gives you all sorts of Delve-ish stuff. You can see emails, events, files, etc. that are linked to that person. You also can see their LinkedIN profile. It’s such a powerful tool to have on a mobile device. Sure, it’s not as good as People Search, but it is a very useful tool that drives the user experience we all strive for.

My main issue that I have with the user experience of Outlook is a lack of customization. Their customization/configuration is focused on data protection, which makes you fall a bit flat here. Ironically enough the only supported items that Intune gives you are:

• Focused Inbox
• Touch ID/Fingerprint
• Save Contacts
• Discover Feed
• Suggested Replies
• Default Signature
• Play My Emails
• Block External Images

Closing Thoughts on User Experience

A few closing thoughts on user experience. Overall, I feel like Boxer does have a slight edge, but realistically you cannot match the user experience for companies using Office 365. It’s near impossible to close the gap that is created without Graph API implementation. Boxer does a marvelous job on a number of feature that I highlighted, but it’s disappointing that they are not covering must haves for 90% of enterprises.

Integrations

Integrations with these products are on completely different spectrums. Microsoft heavily relies on add-ins which is the Microsoft way. VMware Boxer outside of Content Locker relies heavily on the WS1 Intelligence product called Mobile Flows.

Integrations with VMware Boxer

You can slice integrations with Boxer into a few buckets: phishing/spam, enterprise content, and Mobile Flows. We will cover these each briefly.

Enterprise Content in VMware Boxer

Enterprise Content in VMware Boxer is a seamless way of accessing your content without leaving the application. It’s VMware’s answer for OneDrive integration with Office 365. You can configure it with the keys here. I am going to be very transparent when it comes to this. I do NOT believe or support this feature.

Enterprise Content is a nice idea, but the problem is you need to enable SSO for Boxer, which requires the user to set a passcode, which just doesn’t vibe with a good user experience.

It’s very unfortunate because I love the feature, but until they solve that problem it will be a subpar feature. The feature itself is great because you seamlessly access repositories within Boxer from WS1 Content, which encompasses SharePoint, OneDrive, NAS shares, and other WebDAV compliant shares.

Phishing and Spam in VMware Boxer

This is a new and popular feature that you have available now. You give people the ability to report spam and phishing emails inside of Boxer, which will forward those emails to email addresses that you configure. You can even configure Boxer to delete spam after forwarding it over.

Mobile Flows

I won’t waste too much time on Mobile Flows as they could keep me here for a few hours. Below, you can see a demo. Essentially, mobile flows allow you to add in things like approvals for several apps like ServiceNow, JIRA, and WorkDay just to name a few.

Normally this required micro-services and code that you host/build to deliver Mobile Flows, but VMware continues to add ones that will work as COTS solutions.

Integrations with Outlook

Outlook offers two types of integrations. They offer calendar apps and add-ins. We only have 3 choices for calendar apps today with Evernote, Facebook, and Meetup. The Add-Ins will cover more ground.

Outlook Add-Ins

The brilliant thing with Office 365 is that you now have cloud-based Add-ins, such as Zoom, Box, Concur, JIRA, etc. I will admit some of them are really confusing. One of the things that is bizarre to me is you need to click the triple dots inside of an email to bring up JIRA.

The functionality is great and you don’t have to do much to get them working. Provided a company supports an Outlook Web Add-in, it will usually work on the mobile client also. You can see that I can report this suspicious VMware for this email that is clearly phishing.

My top add-ins that I like are:

• Giphy
• Box
• Concur
• FedEx Tracking
• Jira Cloud
• OneNote
• Slack for Outlook
• Translator and much more!

Closing Thoughts on Integrations

It’s too bad that Mobile Flows are a premium feature that requires a WS1 enterprise license because they are quite compelling. A one-stop shop for approvals is a game-changer especially considering how confusing Add-Ins are inside of Outlook.

IT power users will love Outlook for iOS add-ins but most people will be confused as hell. The concepts are nice but the follow-through hurts your user experience and you just can’t explain it away. Microsoft has done so much to make Outlook for iOS similar to the desktop, but they apparently forgot about this one.

I will keep banging my drum about Enterprise Content in Boxer because it’s something that kills them with Office 365 users. There is literally zero reason that any MDM-managed device should have a passcode on Boxer, which is required to make this work. I will pray that one day they will address this.

Security Capabilities

Security Capabilities are a huge gap on the Microsoft side. They tend to be a bit more generic. We will simply just list them and you can infer from them. Let’s start with Microsoft as its easier.

Outlook Security Capabilities

• Block iCloud Backup
• Send Org Data to Other Apps
• Exempt Apps from Org Data Sharing
• Save Copies of Org Data
• Receive Data from Other Apps
• Restrict Cut, Copy, Paste
• 3rd Party Keyboards
• Encryption
• Sync App with Native Contacts App
• Printing
• Restricting Web Content Transfer with other Apps
• Org Data Notifications

As you can see, fairly generic. Infer from that what you will.

Boxer Security Capabilities

Boxer has many more than Outlook as it’s more enterprise security-focused. Let’s list those out to keep it simple:

• Copy and Paste
• Local Calendars
• Personal Contacts
• Printing
• 3rd Party Keyboards
• Insecure connections (HTTP)
• Restrict/Whitelist Sharing
• Secure Open-In
• 3rd party file sharing e.g. Box
• Personal Accounts
• Restrict/Force Hyperlinks to open in WS1 Web
• Email Classification

Pop-Ups and Callouts for External Addresses are one other item that I like to call out. It’s a huge DLP feature that they offer. They mark the email address in red and you even get a pop-up to make sure you really want to send that message!

It’s certainly possible that I missed a few, but you can access the admin guide here for more information. It’s a useful resource and not always easy to locate.

Thoughts on Security

Let’s be honest with ourselves. Microsoft Application Management or whatever term you want to use now is a half-baked solution. It’s never been built to fit the application, but is moreso a broad concept. This hurts them in certain aspects. I expect to be able to lock down a mobile email application properly. That just doesn’t happen here.

So Who Wins?!

So that is the question who is the victor? Who really comes out on top with a best-in-class solution?

The answer is that no one does. Both apps are solid and both have issues. From my perspective, if you are keeping Exchange in-house, you can do no better than Boxer. It does an amazing job with many proprietary features to deliver best-in-class email. Outlook edges them by a bunch in Exchange Online because of the integrations, Graph API features, and just how the Microsoft ecosystem meshes with its friends.

VMware needs to do better. They cannot make the same mistakes that Cisco has made with WebEx Teams that pushed people toward Microsoft Teams to such a degree that Microsoft certified the Cisco SBC now, which I never imagined would happen. My friends at VMware, you CAN do it, yes you CAN!