Securing your Email with S/MIME

Today we start an awesome mini-series from one of our support gurus, DragonFly, about how S/MIME works in general, with following tutorials on how to implement S/MIME in TouchDown on iOS, Android and Mac platforms.  Check out today’s tutorial on iOS!

Hi,

Dragonfly from NitroDesk support here. In the following, today I’ll be describing how to import and use S/MIME in Touchdown for iOS. Using this functionality you can sign messages, proving that you are the person sending that particular message, and optionally encrypt them, meaning the email will only be readable by people who you have included in the message. Signing provides you with non-repudiation and potentially detect tampering on the fly and encryption prevents unauthorized viewing of the message. This type of functionality is great for keeping your emails safe and ensuring that information’s coming from the right source. (For more information on how S/MIME works, here’s a good tutorial: http://technet.microsoft.com/en-us/library/aa995740%28v=exchg.65%29.aspx) Just know that to send an encrypted email, you need to have the recipient’s public key and vice versa- these can be verified from within Touchdown when that person sends you a signed message. Here’s what you’ll need before you get started:

First, you’ll need a certificate for S/MIME signing and the latest version of Touchdown. To get a certificate for S/MIME, you’ll want to contact your IT team. Also, keep in mind the only two certificate types Touchdown supports is .pfx and .p12. The certificate would need to include the complete chain to the root certificate authority.

If you have your certificate already in IE, but need to export it to your desktop,Here’s how (in IE):

1. Go into the Settings>Internet Options, and clicking on the Content tab.

2. Click on Certificates, and find the one you want to export

3. Click Export. Make sure you choose the option to export the private key and also to include all certificates in the certification path.

4. Choose a file path, and save it.

5. Don’t forget to  remember the password you use to perform the export. This password prevents anyone else from being able to access the certificate. If you’re having difficulty with this process, contact your IT team and see if there’s another way you should be doing it. As with any operations like this, make sure you are staying within your IT team’s best practices so you stay in alignment with any security policies.

6. Once you have your certificate backed up to a file, send that file to your email as an attachment, and you’re ready to go.

Let’s start with the iOS version.

S/MIME for iOS

In this demo, I show how to send an encrypted email to the ‘welovenitrodesk’ account.

First, I want to ensure that I have my certificate for S/MIME, so I find the email with the attached certificate, and view it in the attachment list.

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The attached certificate, note the file type is .pfx. 

After downloading, I click the ‘I’ icon and choose to ‘Import for both.’

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Choose Import for Both.

A password prompt appears.

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Enter your certificate password here that was created when you generated the certificate. 

After entering the correct password (This is set up during certificate exporting from your browser, for help with this  please contact your IT team) it will tell you your certificate has been saved.

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Saved certificate message. 

Now that I have a certificate, I’m ready to send the account  welovenitrodesk an encrypted message:

I click on the tools/options icon and enable Encryption and signing.

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Tools icon to enable encryption signing.

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Enable signing and encryption for the email.

I send the email. If you suddenly see this message (see below), it means you didn’t validate the recipient’s public certificate key from a signed message. (This can also be done over the GAL if your company supports it.) Remember how I said earlier that to send an encrypted email, you need the recipient’s public key? Now I just need to fetch it. Thankfully, a while back welovenitrodesk sent me a signed message, which contains the key.

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Oops!

I find the email where welovenitrodesk sent me the key, and click on the lock icon.

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Welovenitrodesk sent me a signed message.

I click ‘verify signature’ and it verifies.

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Now I can send that encrypted message!

The second time, I attempt to send the encrypted message again. This time it comes through.

Back in welovenitrodesk, after having imported the public certificate and the welovenitrodesk certificate, I check the encrypted message, and am able to successfully decrypt it.

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The signed and encrypted email.

Clicking on the lock icon, I can confirm that it is indeed signed and encrypted.

Hope this helps you get a better understanding on how to use S/MIME functionality with Touchdown for  iOS. If you have any questions, please feel free to contact us at  iossupport@nitrodesk.com for any iOS queries. Be sure to check in on Monday for Part II, SMIME for Android. Thanks for reading!

Touchdown – Getting to know your Diagnostics

Today’s post comes from Dragonfly, our trusty, awesome and beloved iOS Support Guru.

Getting diagnostic information from TouchDown for iOS.

Occasionally during the troubleshooting process, a support technician may request a diagnostic log.  Here’s a visual guide on how to retrieve one from TouchDown for iOS:

There are two locations where you can get diagnostic information from the iOS version of TouchDown.

1. During configuration, which can be useful to determine where TouchDown is failing to connect.
2. The diagnostics menu.

In this blog post, I will cover the two methods of obtaining a diagnostic log.

Obtaining a configuration diagnostic:

When you open TouchDown for the first time, or any time after you reset the database, you will be  prompted to configure. On this screen, there is a toggle to Enable Logging. To get a configuration log, slide that to the ‘on’ position (see red circle below) and enter in your information.iosblog1

In the below screenshot, I intentionally entered wrong information and attempted to configure. Note  that as the configuration fails, there is an option to ‘Copy Log.’  Click that to put a copy of the log on your clipboard. Once you click it, you will get a notification that it has been added to your clipboard.

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As I was unable to configure TouchDown, I entered my gmail account using the device web browser, and opened a new email to send to iossupport@Nitrodesk.com.  After long pressing on the body of the email, an option to paste appears. I click it, and it puts the contents of the diagnostic log into the body of the email:

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After you paste the log into the email, send it to iossupport@nitrodesk.com with a description of the issue so the technicians there can see where the configuration is having issues.

Obtaining a regular diagnostic log:

If the support staff request an iOS diagnostic log of some specific behavior, here is how to retrieve it.  On the main mail screen, tap the circle triangle button, and choose the diagnostics button:

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To ensure you get us a correct log, please tap ‘clear,’ which may return you to the main screen again. Enter diagnostics again via the circle triangle button, and enable logging:

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Go back to TouchDown and perform the action you are having difficulty with.  Return to the diagnostics screen after you are done, and copy the log using the ‘copy’ button. You should receive a notification that it has been copied to the clipboard:

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Open a new email, and long press on the body. An option to paste the log should appear. Select that, and you will have a diagnostic log pasted in the body of an email:

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Thanks for reading and hope this was helpful in describing the different types of diagnostic logging in TouchDown for iOS.

Dragonfly

Tasks in Touchdown for iOS

Today we wanted to touch (no pun intended – well, maybe a little) on how to utilize tasks in iOS.  (not iOS7, we’ll get to that once iOS7 is officially released.  Patience, iphone lovers!)

Open Touchdown and Tap the Tasks button.
touchdowntasks

There are several functions, such as Sort, Filter and Search that I find really critical.

SORT allows you to sort Tasks in the list by:
Subject, Start Date, Due Date or Importance, in either Ascending or descending order.

FILTER
helps you organize your Task list. You can filter by Folder, Category or status such as pending, complete, Overdue or Due today.  I like to have mine set for “due in the next seven days” so I have an overview of all the things I have to get done this week. There are many more options such as “Today AND Overdue Tasks,” etc.  You can totally nerd out on this little detail to make it work for your needs.

SEARCHING FOR TASKS
Open Tasks & pull down on the Tasks bar.
TD tasks
Type in your search criteria.
The best matches for your search criteria will appear below the search bar. Oila!

(To search for Tasks in other folders, Tap the Tasks button, enter search criteria and click search.)

CREATING A NEW TASK

Open TouchDown  and Tap the Tasks button.
Tap the New button and fill in your info!
TD New task

Pretty nifty.  Task away!  (Im off to write in more tasks…)

Want more mini tutorials? You can find them all in one place right here in our Nitrodesk Knowledge Base!