Over the last year, Microsoft has been releasing some great software for the iPhone and iPad. Last year, Microsoft released Word, Excel and PowerPoint — first for the iPad, and then universal versions that also work on the iPhone. Those apps were excellent when they were first introduced, and they have been improved with new features every few months. If you want to work with Word files, Excel spreadsheets or PowerPoint slides, there are no better apps for doing so on the iPhone or iPad. As we started 2015, there was only one major part of the desktop Microsoft Office package that was not yet on iOS: Outlook. That changed last week when Microsoft released the Microsoft Outlook app, a free universal app that works on both the iPad and iPhone.
The Outlook app is actually not a new app at all. In April of 2014, an app called Acompli debuted, a free email app with some innovative features. Microsoft acquired the app on December 1, 2014, and the new Outlook app is — for now — essentially the old Acompli app with a new name. But Microsoft promises updates in the future, and now that Microsoft owns the app, I'm sure that the app will continue to work well with Microsoft Exchange, which is used by so many offices, including law offices. Note, however, that the app doesn't require Exchange; it also works with Gmail, Yahoo Mail and iCloud email.
I never tried the Acompli app, but after using the Outlook app for a few days, I am very impressed. The app includes many useful features that do not exist in the iPhone and iPad built-in Mail app. I start this review by noting the key features of the Outlook app, many of which are great. I then note some of my concerns — especially a potentially serious security concern that might cause attorneys to pause before installing this app. But let's start with the good stuff.
FEATURES
Sending Attachments
The built-in Mail app has support for attachments, but it is limited support. Of course you can read and work with attachments to any email that is sent to you, but if you are initiating an email in the Mail app you cannot start typing a message and then decide that you want to add a file as an attachment, unless that file is a photo or video from your Camera roll. For example, you cannot suddenly decide to attach a Word file to an email that you are typing. Instead, you need to go to another app that can open the Word file, then use that app to create a new email with that file attached.
But in Outlook, any time that you are composing a message, you simply tap the paperclip icon to add one or more attachments to your email. You can add as attachments photos or videos from the Camera Roll (the same thing that you can do in Mail), or you can add attachments from your Dropbox, in which case the file itself is not attached but instead a link is created so that the recipient of your email can click the link to see a preview of the file on Dropbox.com and have the option to download the file.
But the feature that I think many people will like the most is the ability to attach any file that was an attachment to any of your recent emails. This is a feature that I have wanted for a very long time. It makes it easy to forward a document without having to forward an entire email. It also lets you gather attachments from multiple different emails and attach them to the email that you are composing.
Even if Outlook had no other unique features, this one feature alone would make me want to have the Outlook app on my iPhone and iPad to make it easier to add attachments to messages.
Quick Filter
Just above the list of emails, there is a button called Quick Filter. Tap that button and you have three choices: Unread, Flagged and Files. Tapping Unread will instantly show you only the unread emails in your Inbox (or whatever folder you happen to be viewing). Tapping Flagged instantly shows you flagged messages.
But the most useful one (for me) is Files. Tapping that button immediately shows you only the email that have files attached. Sometimes I am looking at my email specifically because I want to find an email that had a file attached. It takes less than a second to tap Quick Filter and then tap Files, and suddenly I am only seeing the emails that have files attached, making it that much faster to find the email that I needed.
Files
Speaking of files, one of my favorite buttons in Outlook is the Files button at the middle of the bottom of the screen. Tapping this button instantly shows you a list of attachments in your recent email messages, listed in order of when the email with the files was sent to you, with the most recent ones near the top.
I often open the Mail app not because I want to find an email but instead because I just need to get a file that was attached to a recent email. This single button makes that task incredibly fast. Tap on an attachment and you see a preview of it, and you can then attach that file to a new email, save that file to a cloud service such as Dropbox or iCloud, or share the file by opening it in another app.
Calendar Integration
Outlook is an email client, but it also integrates with your calendar. Yes, this means that you can view your calendar from within the Outlook app, just by tapping the Calendar button at the bottom of the screen. But at least in its current version, Outlook does not does not replace the need to use the built-in Calendar app or full-featured third-party calendar apps such as the excellent Fantastical. For example, you cannot edit a calendar entry in Outlook, although you can create a new one. Instead, Outlook integrates the calendar features that you are most likely to want to use when you are handling emails.
For example, if you need to tell someone in an email when you would be available for a meeting, you can tap the calendar icon (which is close to the attachments icon), then look at your calendar to see your upcoming appointments. Tap one or more 30 minute intervals on your calendar, and if you select contiguous times the app will merge them, so if you tap 3pm and 3:30 the app will understand that you are available from 3pm to 4pm. (You can only select 30 minute intervals, so you cannot indicate availability starting at 3:15.) Then hit Done. This creates an email with a table indicating when you would be available for a meeting. It looks like this:
In the past, I have never had a problem switching from the Mail app to a calendar app to look at my schedule, and then going back to the Mail app to type when I am available. But the calendar integration in Outlook is certainly fast and easy to use, and I suppose that the table that it creates looks nice.
People
The Outlook app looks at all of the people with whom you send and receive email and creates a list of important people. Tap the People icon at the bottom of the screen and you are presented with a list of the recent people with whom you have interacted. Tap a person's name and you will see all of the recent emails that you received from or sent to that person. And thanks to the calendar integration and advanced file features, you can also see a list of upcoming meetings that you have with that person and files that you have received from that person. You can also tap the compose icon on the right near a person's name to send that person an email without having to start typing their name in the To field.
Swipe Gestures
The built-in Mail app has useful swipe gestures, such as the ability to swipe to the left on a message in the list of messages to delete. You have some control over these gestures by going to Settings -> Mail, Contacts, Calendars -> Swipe Options. This lets you assign to swipe left or swipe right the functions of mark as read, flag and archive.
Outlook has even more swipe gesture options and give you greater control over customizing them. Tap the Settings button at the bottom right of Outlook and tap Swipe Options. From here, you can assign to swipe left or swipe right the following options: None, Archive, Delete, Schedule, Move, Mark as Read/Unread and Flag.
Schedule
One interesting function in Outlook is the Schedule function, a function that makes an email go away for a period of time and come back to you later.
You can access this function by assigning it to a swipe gesture, or you can initiate it whenever you are viewing a message in your Inbox by tapping the icon at the top with a triangle in a circle (the same place where you can opt to move a message to another folder or mark the message as unread). Then choose whether you want the message to come back in a few hours, this evening, tomorrow morning, or at a specific time and date that you select.
When you schedule a message, the message is moved out of your Inbox and moved into a special folder on your mail server called Schedule. Then, at the time you select, the Outlook app moves the message back to the Inbox, marks it unread, and places at the top of your Inbox with a clock icon next to it — an indication that the message is not really the most recent message, but instead that it appears at the top because it is being delivered pursuant to a schedule. There have been many times when I have received an email and knew that I would have to deal with it later, so it is interesting to see a function devoted to this specific need. In the past I have simply kept the message marked unread to remind me to go back to it later, but the Outlook approach does seem better.
Note that if you view your Inbox using the built-in Mail app, or using your computer, before the designated time, you won't see the message in your Inbox at all. Instead you need to open the Schedule folder that the Outlook app crates in your Inbox and the message will be in there. At the designated time, while the message will appear at the top of the list of Inbox messages in the Outlook app, if you instead view your Inbox using the built-in Mail app, the message will appear in normal date order. It will be marked unread so that should remind you that you still need to read it, but the Schedule function works best if you continue to use the Outlook app.
Send Location
When you are composing an email, the third icon next to the attachment and calendar icons is a location icon. Tap that button and Outlook will figure out where you are currently located and send a small map with a picture of your current location and the street address of your current location. This is certainly a very fast way of telling someone else where you are located without you needing to type an address. I haven't yet decided how useful this feature will be for me, but if you want a very fast way to send someone your current location, you'll like this feature.
Focused Inbox
One interesting feature of Outlook is that it can provide you with a Focused Inbox. If this feature is turned on in Settings, then when you are looking at your Inbox you will see at the top the words "Focused" and "Other." When you are in the Focused view, you only see the emails that the Outlook app considers to be the most important. To see the other messages in your Inbox that are not in the Focused view, tap Other. It looks to me like Outlook mainly takes mailing lists and emails from vendors and puts them in the Other view, whereas emails from "real" people go into the Focused view.
This is a very interesting feature, but I have to admit that I didn't much care for it I don't like the idea of Outlook telling me what is important and what is not important. I'd rather see all of my Inbox emails in one place and then I can decide whether I don't need to read an email right now. But I recognize that others might like this feature more than I do. For example, I was trading messages this weekend with Ohio attorney Chad Burton, and he told me that he has been using the Acompli app for some time, and now uses the Outlook app, and he loves this feature. He mentioned that he has the app configured so that he only gets notifications when he has a Focused email, not when he receives an Other email. That way, a new email from a merchant advertising a sale, an evite invitation, mailing list emails, etc. will not result in a notification, but an email sent from a "real" person will pop-up a notification of a new email.
If you like this feature, then you will appreciate it being included in Outlook. But if it is not for you, it is easy to turn this feature off, just by using the Settings button in the app. Try it and see what you think.
PROBLEMS
While Outlook has some great features, there are a few problems, or at least potential problems, with this app.
Bugs
Quite a few times, the app froze when I was using it. It never caused me to lose any data, and I was always able to force quit the app and get back to work. Hopefully these bugs will be ironed out in the future, but it is annoying that they are there at all. Apple's own Mail app has been rock solid for me even though I use it all of the time.
Security
This is my biggest concern about the app, and it is one that I still don't feel I have gotten to the bottom of. In fact, I am posting this review today not only so that you know about the features of this app, but also because I hope to get feedback from others on this issue.
First, it appears that the Outlook app, like the old Acompli app, gets your emails from your mail server and then the emails pass through an Acompli (now, Microsoft) server before the email is delivered to your device. I believe that this means that all of your emails, attachments, calendar items, and contacts pass through the company's server. Here is how Acompli explains it on the Privacy page of its website:
We provide a service that indexes and accelerates delivery of your email to your device. That means that our service retrieves your incoming and outgoing email messages and securely pushes them to the app on your device. Similarly, the service retrieves the calendar data and address book contacts associated with your email account and securely pushes those to the app on your device. Those messages, calendar events, and contacts, along with their associated metadata, may be temporarily stored and indexed securely both in our servers and locally on the app on your device. If your emails have attachments and you request to open them in our app, the service retrieves them from the mail server, securely stores them temporarily on our servers, and delivers them to the app.
I don't have a problem with storing my email on my iPhone, but storing my email (and calendar events) on Acompli's website — which that paragraph says that Acompli "may" be doing — raises some red flags me. Acompli has a Security page on its website that states that full security measures are on place while its servers touch your data, including TLS encryption when the information is in transit and hardware accelerated encryption while the data is stored on its servers. That sounds good, but I feel like I need more information to understand the potential security risks here.
Second, there may be a security issue with Acompli storing your email address and password on its server. App developer René Winkelmeyer has a series of posts (1, 2) in which he discusses this risk, and his first post was reported on by Zack Whittacker of ZDNet.
The folks at Microsoft are smart and generally have a good understanding of corporate security needs, so at this point I feel like I need to lean more. For example, an article by Tony Remond of WindowsIT Pro suggests that the security concerns noted above are overblown. Remond quotes from a new document prepared by Javier Soltero, who had been the CEO of Acompli and is now leading the development effort for the Outlook apps at Microsoft, in which Soltero explains how Microsoft is addressing security issues with the app. For example, as for the security of providing the app your Exchange password, Soltero says: "This architecture means that in order to gain access to your password, you would have to have access to both our cloud service and have physical access to the unlocked device." And as for what information is stores on the Acompli/Microsoft server, he says that "we store a subset of email, calendar information and files in a cloud service to facilitate fast, secure delivery down to the device."
Perhaps the security risks are not as large as I fear. But obviously, lawyer emails and attachments often contain very confidential and privileged information, so lawyers need to think long and hard about who has access to them. I realize that many lawyers use services like Gmail every day to store their confidential communications, and they don't have a problem with Google having at least the theoretical ability to read the content of those emails. At this point, I simply recommend that you keep the potential security risks in mind as you consider whether to use this app. And this is an issue that I intend to continue to research.
Other Issues
I've noticed a few additional, minor, issues as I have used this app over the last few days.
Like the built-in Mail app, Outlook for iOS does not show you when a message is marked as important (which shows up as an exclamation point on the desktop software), nor can you mark as important a message you are sending from the Outlook app.
In the built-in Mail app, you can choose whether or not you want to organize related messages by thread. (Settings -> Mail, Contacts, Calendars -> Organize by Thread) In Outlook, you cannot control this feature. Messages are always organized by thread, and when you tap a message to read it the related messages are indicated in abbreviated format either above or below the message that you are reading depending upon whether they were sent earlier or later. If you like the Organize by Thread feature, the way that Outlook handles it makes sense. But if you don't like this feature, you are stuck with it in Outlook.
CONCLUSION
Although Outlook could be a replacement for the iPhone and iPad's built-in Mail app, I think it is most powerful as a supplement to those apps. For example, I can see it being the go-to app for when you want more control for working with attachments. At this point, however, I still need to get my arms around the privacy and security issues before I can recommend this app. If you have thoughts on these issues, I'd love to hear from you, either via email or in a comment to this post, and I can update this post if I get additional information on this topic.
Click here to get Microsoft Outlook (free): 
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