Last year, we revisited Boxer vs. Outlook on iOS to see where they stack up. I know #COVID and all, but let’s see if they caught up at all or if Outlook is distancing themselves further on the race for the top email client on iOS. We will recap email, calendar, contacts, ActiveSync, user experience, security capabilities, and integrations. First, let’s quickly cover the new capabilities that Boxer released in 2021 before going into how they may relate!

New Boxer Capabilities in 2021

Let’s start by listing a short collection of the new features that came out in 2021. We will highlight the ones that I think matter after that:

• Set Boxer as the Default Mail App
• Attach Multiple Photos
• New Files UI
• Teams Online Meeting Integration**
• Calendar Event Notes in HTML
• Disable Files
• Setting to use WKWebView instead of SFSafariViewController for Modern Auth**
• Pre-filling username/email in Office 365 Login Prompts
• Setting Emails as High Priority
• Block External Images in Email**
• Require Email Classification for External Recipients**
• Send S/MIME to DLs
• Add Copy Function to Contacts
• Confirm Opening External Links
• CBA for Modern Auth in Standalone Mode

Stuff with ** are items that require managed app config keys to be deployed as highlighted in the Boxer Admin Guide. I think the two main items that I want to hit on are the Teams integration and the External Email Security.

Boxer and Teams Integration

Enabling the Teams integration is pretty easy. You just need to deploy this app config key:

Key Name: EnableTeamsOnlineMeetings Boolean: True

Once you set that key, you will be able to easily create Teams Meetings in Boxer as you can see from the video below:

Boxer External Email/Web Security Enhancements

Another major focus presumably with ransomware and everything else are new enhancements on the email and web security side.

You can now deliver via app config keys a few big items I mentioned above:

• Confirm Opening External/Untrusted Links
• Require Classification for External Recipients
• Block External Images in Email

All of these settings can be set with Managed App Config Keys providing a stronger security landscape:

Key Name: ExternalLinksAllowlist String: synterex.com
Key Name: PolicyClassMarkingsRequired Integer: 2
Key Name: PolicyBlockExternalImages Boolean: True

The only disappointment I have on this is that many of the new features in 2021 require managed app config instead of using the rich UI configuration they have provided for most features now:

Email Capabilities for Boxer and Outlook

Let’s recap the email capabilities for Boxer and Outlook along with adding in a few new features that improve that experience.

Boxer’s Email Capabilities

As we mentioned last year, Boxer does some great things around email like “Custom Mailboxes” which let you create secondary containers for your sub-folders:

They also offer quick templates to handle quick replies:

On top of that, they’re the only platform that can offer email container synchronization while locked courtesy of FastSync, which I have written extensively about in my ENSv2 article and my FastSync article.

Let’s hit on a few of the great new things they introduced:

Boxer unfortunately did not make any progress on the stuff that I was critical of last year: Office 365 Graph API integration. Come on guys! We NEED Group and Focused Inbox to make this app relevant for the 90%+ of people using Exchange Online now. That is a major shortcoming at this point.

Outlook’s Email Capabilities

As I said last year, Microsoft does a great job in its simplicity. One of the areas that VMware should take a hint from is their email formatting stuff that has hit in more recent months. It is huge to be able to type an email just like you would on a PC in our COVID world now:

It certainly seems on straight capabilities that Outlook is strengthening their position. VMware had a few nice improvements, but not the ones that they really needed here.

Calendar Capabilities for Boxer and Outlook

Let’s recap the calendar capabilities for Boxer and Outlook along with adding in a few new features that improve that experience.

Boxer last year beat them because:

• Supports a default event length setting when creating new invites
• Supports local calendar synchronization/visibility

Outlook had a few items last year that were better were:

• Separate alerts for All-Day Events
• Better User Availability UI/User Experience Design

Fast-forwarding to this year, VMware still has the same issues with user availability, but they did add an interesting new feature.

The new “End Event Early” feature is a great idea by VMware to promote mindfulness in creating meetings. The one criticism is that you cannot configure it via App Config Keys at this point, but it’s a really good idea (should have been in the release notes!):

One other nice feature that VMware introduced is HTML notes for Calendar items, which I think is helpful and was a nice side effect of the Teams integration.

Microsoft’s new introduction to Calendaring is “Workspace Booking” which you can read more about here. Essentially, you can book temporary office locations and tie directly into your Facility Management System. You can see a few of the cool capabilities below:

Contacts Capabilities for Boxer and Outlook

Let’s recap the contacts capabilities for Boxer and Outlook along with adding in a few new features that improve that experience.

As I mentioned last year:

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 Microsofts 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.

Nothing has really changed all that much. We now have the deeper LinkedIN integration inside of Outlook but both are mostly the same.

Overall Thoughts on Core ActiveSync Features

Overall, we can clearly see for Exchange Online that VMware is still behind and I think that lead is growing. They need to execute and hit parity with Outlook because they have so much potential, but it is still falling short.

Microsoft has done a nice job to add some much needed remote work capabilities like HTML support and playing back emails.

User Experience for Boxer and Outlook

Let’s take a few minutes and recap User Experience and cover anything new that has surfaced.

Boxer’s User Experience

Boxer builds a great ergonomic user experience with a few pillars:

They do a number of things well like:

• 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.

The User Experience gaps still exist in 2021. You can configure phishing as a quick action within the app itself, but cannot push that down from WS1. The meeting invite windows are also still a big frustration area:

Nothing major has changed from a straight user experience perspective. They didn’t need to make major changes, but I do think some of their email changes have improved the user experience for the better.

Outlook’s User Experience

Outlook is the king of user experience. You can see a few of their capabilities below.

Their UX is based on leveraging Delve/Graph API to bring fluidity and grace to access of data. They really hit all of the notes of great consumer user experience:

Their problem similar to last year is a lack of customization. They did make some major improvements though. You can access those docs here. The stuff you can customize is:

• Focused Inbox
• Touch ID/Fingerprint
• Save Contacts
• External Recipients MailTip**
• Organize Mail by Thread**
• Native Calendar Sync**
• Text Prediction**
• Themes**
• Discover Feed
• Suggested Replies
• Default Signature
• Play My Emails
• Block External Images

One other area that I neglected last year, which I think is more prevalent are Outlook’s tool tips. VMware could really take some tips here. By clicking on the question mark icon, Outlook takes you to the Microsoft documentation to explain the feature to you. GREAT GREAT JOB MICROSOFT!

Final Thoughts on User Experience

Both Boxer and Outlook were already doing a great job here. Microsoft probably advanced themselves further with things like text prediction, play my emails, and more. There is no surprise why both platforms have a strong following.

Integrations for Boxer and Outlook

Let’s cover the Integrations quickly as I have some great news to report.

Integrations with Boxer

Last year, I was super critical of Enterprise Content, but I am VERY happy to report that you can finally use it without destroying the user experience. As mentioned earlier, they have done a great job of making it seamless via attach. Let’s check the demo!

We also still have the other great integrations with Mobile Flows and Spam/Phishing that we covered last year:

Integrations with Outlook

Outlook integrations are still the same situation with adding in “Add-Ins” like we do with Outlook:

This year, my list of top add-ins are:

• Box
• Concur Expense
• Evernote
• FedEx Tracking
• Gfycat
• iPlanner Pro
• Jira Cloud
• OneNote
• Slack
• Smartsheet
• Translator
• Trello
• Wrike
• Zoom

Final Thoughts on Integrations

As more customers are moving toward WS1 Enterprise licensing, Mobile Flows has been picking up steam. The Boomi integration to replace Mobile Flows in the near future should evolve that even further. VMware made a big leap forward with finally fixing Enterprise Content.

Outlook just isn’t the place for integrations. Microsoft Teams really owns that arena. The add-ins are nice but VMware is working hard on making Boxer a strong integrator.

Security for Boxer and Outlook

Last year we covered what they can actually do:

Outlook Security	Boxer Security
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	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 External Address Warnings

This year as I mentioned earlier, VMware added a few new ones:

• Disable Files
• Setting to use WKWebView instead of SFSafariViewController for Modern Auth
• Pre-filling username/email in Office 365 Login Prompts
• Block External Images in Email
• Require Email Classification for External Recipients
• Send S/MIME to DLs
• Confirm Opening External Links
• CBA for Modern Auth in Standalone Mode

VMware does continue to do a nice job on layering security capabilities. Microsoft has settled pretty safely into their core security controls for Outlook. They did a few small ones like a character limit for cut and copy. They have also introduced conditional launch for App Protection Policies to block access for a few conditions:

Final Thoughts on Security

Lets be honest with ourselves. App Protection Policies is still a half-baked solution. Its never been built to fit the application, but is more so a broad concept. This hurts them in certain aspects. I expect to be able to lock down a mobile email application properly. That just doesnt happen here. It works for them and people are happy, but it doesn’t mean they’re right.

Some Closing Remarks

It drove me crazy how Gartner claims that Microsoft did such an amazing job executing their vision in 2021. It’s probably hard to say if they really did. I think we could honestly say that the pandemic slowed progress, but when you look at Boxer it really took its toll. They had a much better year in 2020 with minimal progress this year.

I hope VMware makes some progress because I have always felt that Boxer has tremendous potential. Sure, they did make some nice inroads, but they need to finish their Graph implementation because its hard for me to argue with Gartner that execution fell a bit short in 2021.