Outlook 2016 How Does Outlook Keep Track of Received a Message So That It Does Not Download It Again

Did you lot know that the Microsoft Outlook desktop application offers 3 methods to encrypt emails, including the latest OME pick that does not require installing certificates and lets y'all send encrypted email to external recipients (such every bit free spider web mail users on Gmail, Yahoo! Mail, or whatever other email account)?

Questions: Which email encryption options are available in your scenario and which one should you choose? How practise you lot gear up your selected encryption option and get started sending and receiving secure email? How practise you obtain encryption certificates for Outlook, for yourself and your recipients? Which pick gives you the Outlook Encrypt push?

Which of the 3 Outlook e-mail encryption options are available to you depends on who your recipient is and which email business relationship you are using to send encrypted e-mail. The three options and their availability scenarios are:

1. Using digital IDs (certificates) for sender and recipients (S/Mime): This selection works with whatever email business relationship that you have added to Outlook but requires your recipients to also utilize Outlook (or an S/Mime uniform email awarding). Both you and your email recipients must also install and share encryption certificates. This option is non bachelor for you if you need to send encrypted email to free webmail users such as clients on Gmail, Yahoo, iCloud etc.
2. Role 365 Bulletin Encryption (OME): This pick does not require installing certificates and allows you to send encrypted messages to whatever e-mail recipient. However, this pick is only available to you if y'all utilise an Office 365 email account (Substitution Online). As well, yous need the Outlook application installed every bit part of the Role 365 subscription (this encryption option is not bachelor in Outlook 2013, Outlook 2016, or Microsoft Office once license purchases). This choice is also likely the most expensive.
3. Using Email Encryption Add-ins: The right Outlook email encryption add-in can allow you lot ship encrypted to any recipient (any email address, including free webmail users) using any email account. And so this choice to encrypt email in Outlook combines the best of both the previous 2 options. Likewise, this is likely the lowest cost option, or even gratis.

The all-time Outlook email encryption option for you among the available ones depends on the ease of utilize for you and your recipients, available features such equally access to encrypted messages outside Outlook, costs, and other capabilities. The tabular array below summarizes the features to help you choose.

If yous already know the one you desire and only need the encryption setup instructions or the steps to send a secure email in Outlook:
- Jump to Method 1: Using digital ID (encryption certificates) and South/Mime
- Spring to Method 2: Using OME
- Jump to Method 3: Using costless encryption add-ins.

	Using Certificates (S/Mime)	Office 365 Bulletin Encryption (OME)	Add together-ins (due east.g. Encyro Outlook Addin)
Which email accounts can y'all send from	Many: Most electronic mail accounts that work in Outlook (but non G-Suite with GSSMO).	Only Microsoft: Part 365 Exchange Online only.	Many: Most e-mail accounts that work in Outlook.
Is initial setup difficult	Very Hard: Both you lot and your recipients must purchase and install certificates.	Like shooting fish in a barrel: Upgrade to the correct Office 365 subscription.	Easy: Install add-in.
How hard to ship encrypted	Moderately Easy (vi clicks): Select Options -> More Options -> Security Settings -> Encrypt -> OK -> Send.	Moderately Easy (3 clicks): Select Options -> Encrypt -> Send.	Piece of cake (1 click): Click Secure Send.
How hard for recipient to open your encrypted e-mail	Like shooting fish in a barrel: Once initial setup performed, encrypted emails open ordinarily.	Moderately Hard: Recipient must asking a new code each fourth dimension, wait for code in email and so enter lawmaking to open your secure email.	Easy: Recipient tin can open with one click (link auto-expires for security).
Can y'all receive secure replies	Aye: Since recipient likewise installed certificate, they can send encrypted.	Yes: Secure message view offers option to respond.	Yes: Secure message view offers selection to reply.
Can recipient forward	No: Unless they assistance forwardee install certificate.	Yes: Encryption applies.	Yes: Encryption applies.
Tin you receive a new secure message from clients	Yes: Since recipient also installed certificate, they can send encrypted.	No: They cannot start a new encrypted email.	Aye: Yes, for Encyro Outlook Addin (varies for other add-ins).
Read secure letters exterior Outlook (due east.g. on mobile)	No: Need admission to your PC with Outlook and certificates installed.	Yes: Tin can access via outlook.com.	Yes: Yes, for Encyro Outlook Addin (varies for other add-ins).
Cost	Expensive: $forty-$370 per year for certificate for you. As well need certificate for each recipient.	Expensive: $8-xv/month ($96-180/year) extra on top of your O365 Business concern Essentials or Business concern Premium subscription.	Complimentary: Gratuitous for Encyro Outlook Addin (varies for other add-ins).
Overall ease of use	Difficult: Setup is not possible for many clients.	Moderate: Receiving your secure message is hard. You must use Microsoft email.	Easy: Like shooting fish in a barrel for you and your clients.
Recommended for	Sending to government agencies or enterprises that use Outlook and have certificates setup.	Sending to your vendors or others where you lot can mandate your requirements.	Sending to clients on different email services such every bit Gmail, Yahoo, Hotmail, iCloud and others.

Every bit the table shows, the S/Mime method is just suitable if your recipients also use Outlook and are willing to install certificates. If your recipients practise use Outlook merely you have to buy certificates for them, this option becomes extremely expensive. This choice should primarily be called if your recipient's organization requires it.

The OME selection is slap-up if you already employ Microsoft email through an Office 365 subscription and practise not mind recipients to go through the extra pace of requesting a lawmaking. In practice this can be a hurdle that many clients may need mitt-property with.

The option to utilize the Encyro Outlook Addin provides the easiest user experience and is costless.

Regardless of which option you cull, yous can find the setup instructions and the detailed steps to send an encrypted e-mail from Outlook, below.

Microsoft's instructions to encrypt e-mail in Outlook tin can be a picayune daunting as the different steps to obtain email encryption certificates and using the available options are split across multiple documents. Equally a result, others have attempted to explain how to encrypt e-mail in Outlook, such as in these articles by TutsPlus, Comparitech, LaptopMag, SSLSupportDesk and TrendMicro. Unfortunately, these articles take not been updated to include the easier OME option that newer versions of Outlook provide. Also, about of them show older screenshots from Outlook with the "Become Digital ID" push button to obtain electronic mail encryption certificates. This push button is no longer available in Outlook 2016, Outlook 2019 and Outlook ProPlus (the version installed with an Office 365 subscription). In this article, we want to provide the most up to appointment information to help y'all brand the correct choice for your business email encryption in Outlook, and give you lot comprehensive setup instructions with screenshots.

Method 1: Using Certificates (South/Mime)

The sections below walk yous through all the setup instructions including the procedure to obtain the required email encryption certificates.

Initial Setup

The key steps to setup email encryption using the S/Mime option are:

1. Obtain an email encryption certificate for yourself, import it in Outlook, and share it with your recipient.
2. Ensure that each of your recipients has an email encryption certificate installed in Outlook (or other S/Mime uniform email application) at their stop, and take them share it with you lot.
3. Learn the steps to ship an encrypted e-mail.

Purchase Certificate: You may obtain a document from several document regime. Microsoft'due south documentation recommends iii document regime (CAs):

Equally of this writing, following the links in the Microsoft document above, we found that the Comodo certificate was priced at $48/year, GlobalSign at $369/twelvemonth and IdenTrust at $39 or $79 (depending on individual or business). To purchase, click this Microsoft link and then click on the CA of your option.

You lot could purchase the certificate from other CAs equally well: be certain to select the e-mail security certificate (sometimes also called an S/Mime encryption certificate, or secure email certificate) and not the SSL document which is likely the one most prominently advertised on the CA's website. Here is a link to obtain a free email security certificate.

When y'all purchase a document, you will receive a file containing the document and a password that is required to import the certificate.

Backup the document and countersign: Make certain yous maintain a backup of both the certificate file and the password because in example your computer or hd gets damaged and you need to setup Outlook email encryption on a new calculator, you will need this same document once more. If the certificate is lost, then y'all volition not be able to open your previously sent or received encrypted e-mail. Also, if you change to a new document, all your email recipients who take your sometime certificate will be required to update to the new one, which could be a very laborious process for yous.

Import Document in Outlook: In one case you take purchased (and backed up!) the document, open or get to the Outlook awarding on your computer and follow these steps:

• Click File in the height left.

• Click Options.

• In the new window that opens, click Trust Center.

• Click Trust Centre Settings.

• Click Email Security in the left pane.

• Nether the heading Digital IDs (Certificates), click Import/Consign. (Notation: If the certificate was not purchased by you simply already installed on your reckoner by your admin/IT staff, and so click the "Settings" button instead of "Import/Consign" and then select the required certificate from the options shown. Your IT staff who installed the document should tell yous which certificate amid the options shown should be selected.)

• In the new window that opens, make sure Import existing ID from file is selected. Click Scan and browse to the certificate file (typically a .pfx file) that you obtained when y'all purchased the certificate. Enter the password associated with the document file and click OK.

• You may get a popup like the one shown beneath, informing you that the security level is set to Medium. Information technology is best to leave it at Medium (the but other selection to fix is High but that will require inbound the certificate password more oftentimes). Click OK.

• At this stage, gratis certificates may cause an additional warning to show up, informing you that Windows cannot validate that the certificate is really from the claimed certificate authority. If you get such a warning, and wish to use the certificate anyway, click Yes to keep.
• The Import/Export window will at present shut automatically. Click OK on the Trust Center window to close it.

Your certificate is now imported. Your recipients also need to obtain and import their ain certificates. Feel free to signal them to this link for instructions: https://web log.encyro.com/how-to-encrypt-e-mail-in-outlook/#method-i-using-certificates-s-mime-.

The next step is to share information technology with your recipient(south) and likewise obtain their certificates.

Share your certificate with each recipient: To share your document, send a digitally signed message to each email recipient to whom you intend to send encrypted electronic mail in the future. Hither is how:

• Start composing a new email in Outlook:

• On the new message window, click Options in the tiptop menu bar:

• So click the little icon next to More Options:

• In the new Properties window that opens, click on Security Settings...

• In the Security Properties window that opens, click to select the Add digital signature to this message. Optionally, you may click the Change Settings button to view which certificate is being used for signing the bulletin. It should be the certificate that y'all recently imported. Click OK on this window and then Close on the Properties window.

• Send the message to the intended email recipient(s). In the bulletin trunk, you may wish to include instructions for them to add together your certificate to your contact data in their address book, besides as to ship you a digitally signed message, so you can become their document as well. Experience gratis to point them to this link for instructions: https://blog.encyro.com/how-to-encrypt-electronic mail-in-outlook/#method-1-using-certificates-southward-mime-

At this bespeak, you lot have sent your certificate to your contact(due south). Note that the public cardinal portion of your document is sent - so others can encrypt a bulletin that they need to ship to you. Simply you lot can decrypt such an encrypted email message sent to you because to decrypt, you need your individual cardinal which is imported only inside your Outlook awarding.

How To Send Encrypted

Now, to send an encrypted message to a recipient, you need to have their certificate (public fundamental portion). So assuming your contacts have procured their ain e-mail encryption certificate and have sent you a digitally signed email from their Outlook (or other S/Mime compatible) awarding, follow the steps below to add their certificate to your contact data.

Add together Recipient'due south Certificate to Contact Data: These steps demand to be followed for every electronic mail recipient who volition receive encrypted email from you.

• Open the digitally signed email received from that recipient (your recipient must accept sent you a digitally signed email, signed using their email encryption document).
• In the top expanse where the "From" information for the message is shown, right- click the sender's proper noun and click Add together to Outlook Contacts. If the Contact is already in your contacts, you may use the option to Edit/Update the contact instead of adding a new contact.

• In the contact carte du jour that opens, click Certificates in the tiptop ribbon. Note: In some older versions of Outlook, the full contact card may not open at this footstep - go to the People view in Outlook and and then in the list of contacts shown, double click this contact to open their total contact listing. Once the full contact menu is opened, yous should be able to see the Certificates push in the superlative menu as shown beneath.

• The contact menu should and so show yous a listing of certificates with at least one document for that contact and when you lot select that certificate, it will evidence you lot a message informing you that the certificate can exist used to encrypt messages that yous send to this contact.

Now (finally!) you are all set to send encrypted letters to this contact.

To Ship Encrypted E-mail: Offset a new email bulletin as usual and:

• In the new message window, click Options in the tiptop menu.

• Click the footling icon adjacent to More Options.

• In the Properties window that opens, click Security Settings.

• In the Security Properties window that opens, click the checkbox next to Encrypt message content and attachments. Note that the message subject volition not be encrypted. It is a expert idea to include something in the subject that helps the recipient know what this email is nearly but do not include any sensitive content in the subject. Click OK on this window and then Close on the previous one.

Finish composing your electronic mail bulletin and add any attachments. Click Send as usual to transport the message. It will exist sent encrypted. Any copies of the e-mail message saved on intermediate electronic mail servers are also encrypted since only your recipient has the certificate with the private key to decrypt this message.

Circumspection: The Due south/Mime encryption arroyo suffers from a security vulnerability, known equally the message takeover set on. This vulnerability allows an assailant to intercept your message, and add their own signature impersonating you. While the attacker cannot decrypt your original email, they may exist able to decrypt replies and subsequent emails on that email thread.

How your recipient opens your encrypted electronic mail

If you accept not notwithstanding obtained the certificate for this recipient, and so Outlook volition refuse to send the message. So if the message is sent, you can exist adequately confident that the recipient has the required certificate to open your encrypted email. They may need to be on their desktop figurer and open the message in Outlook (rather than say on their mobile device). Your recipient'south Outlook application will automatically decrypt the message for your recipient.

If your recipient replies to this electronic mail bulletin, the respond will automatically be encrypted (assuming your recipient had added your electronic mail encryption document to their contact data).

Once your recipient has performed the initial setup steps described above, they take the required encryption certificates. They can easily send you encrypted replies by replying to your encrypted email. They tin can also send you new encrypted emails past post-obit the steps to transport an encrypted email described above.

Features and Toll

The pick to encrypt email using certificates (Southward/Mime) is easy to utilize once the initial setup steps of procuring and sharing certificates take been performed.

Still, if you are considering encryption options for your business electronic mail, nosotros recommend this option only for cases where your recipient explicitly asks for such encryption. That is only probable the case if your concern or professional practice serves big enterprise clients or authorities agencies.

If you serve many small businesses or individual clients, it is unlikely that your recipients will take the resources and expertise to purchase and install email encryption certificates. Many may be using free webmail accounts such every bit Gmail, Yahoo and others where the option to install S/Mime certificates is not even bachelor.

Assuming you do apply this selection, as well go along in listen that:

• You will not be able to access your encrypted email outside of Outlook. If for case, you happen to be away from your calculator that has Outlook installed and the email encryption certificates imported, and need to check an urgent secure message received, say, on your mobile device or your spouse'southward computer, that will non be possible.
• Your recipient may not exist able to forward your encrypted email to others. Suppose y'all sent an encrypted email with tax or wellness data and the recipient now needs to forward that data securely to their mortgage broker, business partner, lawyer, or family member. And then, unless their intended forwardee also uses an South/Mime compatible e-mail application (e.g. Outlook) and has an email encryption certificate installed, your recipient will not exist able to forward the information as an encrypted email.
• Yous cannot use South/Mime e-mail encryption with a G-Suite email account if using GSSMO, as documented past Google hither. The workaround is to use IMAP instead of GSSMO but then you practise not get Google calendar to Outlook agenda synchronization and several other dainty features of GSSMO.

Costs: As of this writing, electronic mail encryption certificate costs from the Microsoft recommended document regime ranged from $39 to $369 per year.

The cost of the certificate is a recurring cost as the certificate needs to be renewed every year (or every 2 or 3 years, if you paid for multiple years in accelerate). Also, this is the cost for one certificate: you need a certificate for each user at your arrangement. Your recipients also need to purchase certificates.

Method two: Office 365 Bulletin Encryption (OME)

The OME email encryption option lets you ship an encrypted email to whatsoever electronic mail accost. So your recipient need not be using Outlook or take any email encryption certificates installed. The two restrictions to keep in listen are:

• OME works only with a Microsoft email account, so y'all should be sending from an e-mail account that yous ready as role of your Function 365 subscription (Exchange Online).
• The recipient will have to perform a couple of extra steps each fourth dimension they receive your encrypted email. They will typically have to asking a special code that will arrive in another electronic mail. In one case they receive the 2d email, they will have to manually copy and paste the lawmaking from that email into a box on the web folio that will display their encrypted e-mail. (Detailed steps with screen shots announced further below.)

Initial Setup

To enable Role 365 electronic mail encryption the primal stride is to upgrade your Office 365 subscription to a plan that includes Office 365 Bulletin Encryption. Unfortunately, the pop Office 365 Business Essentials (that provides you with a Microsoft hosted electronic mail service) and the Role 365 Business organization Premium (that additionally includes the installed Office applications including Outlook, PowerPoint, Give-and-take, Excel and others) plans exercise Not include OME. Even Office 365 Enterprise E1 does not include OME.

Every bit specified in Microsoft'due south documentation, you must upgrade to Office 365 Enterprise E3 or E5, Microsoft Enterprise E3 or E5, Microsoft 365 Business, Office 365 A1, A3, or A5, or Office 365 Government G3 or G5. (Alternatively, you may add Azure Data Protection Plan ane to your O365 subscription, but this unremarkably works out to be more than complex for well-nigh users and more expensive as well).

To upgrade:

1. Go to https://www.role.com/ and click Sign In. Sign in with your Function 365 administrator account.
2. In the option tiles shown, click Admin.
3. And so click Billing in left pane, and click Subscriptions under that.
4. Click the Switch Plans push to upgrade to a college plan. The least expensive plan to get OME is Office 365 Enterprise E3 and volition cost $xx/user/month (an additional $viii to $15 per month compared to Office 365 Business concern Premium or Concern Essentials). If the Switch Plans button is non available, see these instructions from Microsoft for alternatives.

One time you upgrade, you can verify that OME is bachelor to y'all as follows.

• Option i: Go to world wide web.outlook.com and sign in as one of the users on your Role 365 subscription. Start composing a new message. The Encrypt push button should show as enabled (not grayed out) in the top card above the new message composition form.

• Option 2: Beginning (or re-start) the Outlook application on your computer. You lot must be using Outlook ProPlus, the version installed as part of your Office 365 subscription (non a version of Outlook installed through a one time purchased Office license such as Outlook 2016). Start composing a New Email. Click Options in the top menu and yous should run across that the Encrypt button is enabled.

At this stage yous are ready to start sending encrypted email using Office 365 Message Encryption (OME).

How to Send Encrypted

Sending an encrypted email is easier than with the document (S/Mime) approach because instead of having to navigate through More Options and Security Settings menus, the Outlook Encrypt button is offered within the Options tab itself on the new message composition window. The steps are:

• Start composing a New E-mail.

• Click Options in the superlative carte du jour and then click Encrypt. (Optionally, you may click the niggling arrow in the lower part of the Encrypt button and choose to also forbid forwarding of the email.)

• You lot should now see a message informing y'all that encryption is applied to this bulletin.

• Finish composing your bulletin and click Send every bit usual to send it.

How your recipient opens your encrypted email

When you transport an encrypted email using OME as above, your recipient receives an electronic mail from you without the actual email content or attachments but with an e-mail body that looks like the one shown below (the formatting of the e-mail may expect a little different depending on which email application or web-mail interface your recipient is using; the screenshot below is from Gmail).

Your recipient will need to click the button Read the bulletin. (The button may show up as a link in sure email applications.)

Upon clicking that button, your recipient will exist taken to a web page that looks like the one below:

Circumspection: The pick to Sign in with a work or school account will only work for your recipient if they have an Function 365 subscription with the aforementioned e-mail address as you lot sent them the message to. This can exist confusing for your recipient because clicking the link to Sign in with a work or school account will work even if the recipient's email is not associated with a relevant Office 365 subscription but after logging in, they will not be able to see your message.

So unless your recipient has an Office 365 subscription with the same email address that yous emailed them at, they should click the link Or, sign in with a one-time passcode.

(For certain recipient email addresses, those on Gmail or Yahoo! Post, the above spider web page will look a piddling different and they will run across a button to login with either Google or Yahoo:

These recipients may click the relevant sign-in option so login with their Yahoo or Google business relationship.)

Afterward your recipient clicks Or, sign in with a ane-fourth dimension passcode, they volition be taken to a second web page that looks like and then:

At this stage, your recipient will need to switch abroad from their web browser and go back to their electronic mail business relationship to look for an email from from Microsoft Office 365 Message Encryption (MicrosoftOffice365@messaging.microsoft.com). Annotation that this email comes from Microsoft'southward email address and not yours, and so your recipient may have to look for it in their spam or junk electronic mail folders if it is non establish in their electronic mail inbox.

The email they receive contains a passcode and looks like the 1 below:

Your recipient would copy the passcode from this email and then go back to the spider web page shown previously that was request for the passcode to exist entered.

Once they enter the passcode and click Continue on that web page, they will finally arrive at your secure email bulletin forth with any attachments. The web page that shows your encrypted message looks similar the 1 beneath.

Clicking an attachment either shows a preview, or in the case of Office files (Word, PowerPoint, Excel etc.), it shows an mistake like the one below:

Your recipient must manually download the file and and so open it.

This can be confusing for your recipient, and is more difficult for them than if you had used the Encyro Outlook Addin in which case the file would have downloaded automatically.

Replies: Your secure message displayed to your recipient has a button that allows them to Reply All (clicking the lilliputian pointer next to Answer All lets them change it to Reply or Forward). Clicking Reply All, Reply, or Forward starts an encrypted response. So your recipient tin can send you a secure response back if needed.

New Secure Electronic mail: There is no option for your clients to ship you a new secure bulletin (other than they purchasing an OME enabled Office 365 subscription of their own). For instance, if yous send an electronic mail request for a sensitive document, the client cannot respond with a secure file in response to your non-encrypted email. (Such an option is bachelor if you apply the Encyro Outlook Addin as explained in Method 3 after in this article.)

Features and Cost

OME is relatively piece of cake to use for the sender. As a sender, yous as well have the reward over using South/Mime or certificate based encryption (Method 1) that you tin admission your secure email outside of Outlook. For instance, if you are away from your computer with Outlook installed, or the reckoner is damaged, you tin can always admission your secure email at outlook.com from a unlike computer or even a mobile device.

Another reward over Method 1 is that you demand non backup any document files or related certificate passwords. In case your calculator is damaged, simply installl Outlook on a new computer and login with your Office 365 account. Your secure messages will remain available.

A third advantage over Method 1 is that your recipient tin likewise frontward your secure message to others and encryption will automatically employ. Your recipient can forrad to any email address without worrying about certificates or other setup to be performed by the political party they are forwarding to.

At the same time, the following limitations should be considered if planning to use OME for your business organisation email encryption:

• Difficulty for recipient: The recipient must request a passcode, switch dorsum and forth betwixt their web browser and their email a couple of times, and manually copy and paste a passcode before they tin read your secure email. These steps can be a hurdle for many recipients, resulting in support calls to your office. (Receiving your message is much easier for your recipient when you use Method three, described further below.)
• Need Outlook ProPlus: The OME email encryption option is only available from Outlook ProPlus, as installed through your Part 365 subscription. If you purchased a Microsoft Office license without the Office 365 subscription, you cannot use OME from Outlook. (Methods 1 and iii work with both Outlook ProPlus and one time licensed versions such equally Outlook 2013, Outlook 2016 and Outlook 2019.)
• Messages do not elapse: OME does not requite you the pick to set a bulletin expiry duration on your secure bulletin. With Method 3 beneath, you can set an expiration period.

Costs: The cost of using OME boils down to the extra money paid for upgrading to an Function 365 plan that supports OME.

• If you already have an Part 365 subscrition at either the Office 365 Business Essentials or Business Premium levels, your toll to upgrade would be $15/month/user or $8/month/user respectively to add the OME capability.
• If you currently have another business email service or are using a free electronic mail service such every bit Gmail, then your cost will be to purchase an Office 365 subscription plan that is at least $xx/month per user.

Depending on your scenario, the toll of using OME adds upwards to an actress $96 to $240 per year, per user. This makes OME one of the more expensive options, especially considering that free alternatives are available, every bit explained in Method three below.

Recommended For: We recommend the OME option for your business email needs if you are either sending secure emails primarily to vendors or others who yous can railroad train to receive your encrypted email, or to recipients who are obliged to follow your security requirements. If sending secure email using OME to clients and customers, especially individual customers without Information technology expertise, you may take to spend extra time helping them open up your encrypted emails, at least the first time around.

Method 3: Outlook Encryption Add together-ins

This is likely the easiest method for pocket-size businesses without defended It staff. It is as well the all-time method to send encrypted messages to recipients who may not have any encryption ready in their own email accounts.

With this option, you can use pretty much whatsoever email account that you lot accept added to Outlook, including a costless email account from Gmail, Yahoo! Mail, or other inexpensive business email providers such as Zoho Mail or Rackspace E-mail (these price less than the Part 365 email service). And you can ship to any email address without requiring your recipient to perform any setup, installation, or business relationship sign upwards.

We offset draw how this option works taking the Encyro Outlook Addin equally an example. Multiple Outlook electronic mail encryption add together-ins are available and we describe some of their differences later in this commodity to help you cull.

Initial Setup

The initial setup typically involves installing the add-in. Yous go to the add together-in's website and download the installer. For Encyro, go to Encyro Outlook Addin and click on the Download push button.

Depending on your browser, you lot will run into an option to run, open, or relieve the file.

For example, in Chrome, clicking the Download button should show the downloaded file named setup.exe about the bottom of your browser window. Click the file itself or the little arrow adjacent to it to see the choice to Open it. Opening it will start the installer.

In Border, yous volition see an selection to Run the downloaded file, once more nearly the bottom of the browser window, as shown beneath.

In FireFox, you lot will likely get an option to Save the installer file:

Afterwards you lot click Save File, go to the downloads icons in the top bar, to the correct of the Firefox address bar and click on the downloaded setup.exe file to run it.

If using Internet Explorer, you will see an selection to Run the downloaded file nigh the bottom of the browser window.

After you click Run or Open or click the downloaded file to execute it, you volition get a prompt to begin the installation. Click Install:

If the in a higher place window does not testify up, information technology may have been hidden by another window on tiptop. Yous should run into an icon for this installer window in the task bar near the lesser of your screen. Click the icon shown below to view the above window and then click Install.

The installation will progress and may accept a minute or so. You may receive a Windows prompt to allow the installation. Once done, you will get the following window. Click Shut.

At this stage, first or restart Outlook. To verify that the installation succeeded, start composing a New E-mail and you should see the Secure Send button as shown below, near the top left:

If the button is not visible, the Message tab may exist collapsed. Click on Bulletin in the top menu:

The you should meet the Secure Send button. To prevent the push from disappearing, click the little push-pivot similar icon towards the extreme right in the Message tab:

Once the Secure Transport push is available, you are ready to send encrypted email using Outlook to whatever email accost.

How to Send Encrypted

Click the New Email push in Outlook. Etch your email as usual and adhere any files you demand to send encrypted. Now, instead clicking the Transport push, click the Secure Send push.

The message content and attachments will be encrypted. But like in Method 1 and Method ii, the subject is not encrypted. The subject helps your recipient know what the electronic mail is about before they get to the decrypted view.

How your recipient opens your encrypted electronic mail

Your recipient gets an email from your email accost, with the subject that you typed just the e-mail body is changed to look like the following:

When your recipient clicks the Access Now button, they will be taken to a web page that shows them the secure message that yous sent, such as:

Different Method 2 (OME), at that place is no dorsum and forth needed between the message web page and email to obtain and enter any passcode. Rather, to maintain security, the message will automatically expire past the time mentioned in the notification e-mail. The sender can change the number of days after which the message expires.

On the web page that displays your secure message:

• The user may view the bulletin and download any attachments.
• Cull to ready a password: For security reasons, the message volition automatically expire, unless the recipient selects the option to fix a password and retain indefinite access.
• Cull to send you a secure respond (once they start the reply process, they could also forrard the message to others and encryption automatically applies).

Note: If the recipient happens to accept an Encyro account (such as because they gear up a password on your previous bulletin and hence obtained a gratuitous Encyro business relationship), then the Access Now button volition take them to their Encyro account login page and and so show them the secure message after they login. If your recipient has forgotten their countersign, they can reset it themselves on the login page without you lot having to reset their account.

Replies: The spider web page that shows your secure message to the recipient also shows them an selection to send a secure reply.

New Secure E-mail: The Encyro Outlook Addin comes with an upload page that allows you to receive secure messages from your clients without asking them to sign upward for any account (see 1 minute demo video). For case, you could send an email (without encryption) to your client request for some sensitive document and yous could simply include your upload page link in your bulletin or your email signature. Your recipient would click that link to transport you lot a new secure message. (This may not exist an option with all Outlook encryption add-ins, but is a feature with the Encyro Outlook Addin).

Features and Cost

The Encyro Outlook Addin makes information technology easy for both the sender and receivers to communicate securely. I advantage of this add-in over Methods 1 and 2 is that with Method 3, sending a secure bulletin requires just one click, as opposed to 5 clicks in Method one (assuming the initial setup has already been done) and iii clicks in Method 3.

A 2d advantage is that this method over method ii is that it makes information technology much easier for your recipient to open your secure message. Simply one click takes them to your secure message as opposed to the multiple dorsum and forth steps required in Method 2.

A third reward over Method 2 is that you can utilize any email account to transport your secure messages, while Method 2 (OME) only works with an Office 365 email service. For case, yous could employ Method 3 with a free email business relationship from Gmail, a gratis email account provided by your website host, or an inexpensive business organisation email account from Zoho, Rackspace or others. An reward over Method i is that you can employ the Encyro Outlook Addin with G-Suite based electronic mail accounts with GSSMO (or IMAP), while S/Mime email encryption does non piece of work with G-Suite using GSSMO.

Costs: The Encyro Outlook Addin is free. A paid tier is available to obtain additional features such equally custom branding, compliance options and audit trails, and system level multi-user controls. However, the free tier suffices to transport secure messages to your clients.

Recommended For: Nosotros recommend Method iii, specifically with the Encyro Outlook Addin, for scenarios where you lot need to transport secure letters to clients who may not themselves apply Outlook and may also utilise gratuitous web-mail service based e-mail accounts such as on Gmail, Yahoo! Mail, Isp (ISP) based electronic mail accounts and then on.

Which Outlook encryption add-in is all-time for me?

If you decide to proceed with Method 3, you have the choice of multiple Microsoft Outlook encryption add-ins, such as from ShareFile, Virtru, Encyro, Jumble, SmartVault, TrendMicro and some others. Largely, the add-ins fall into two types:

1. Stand-alone Add together-ins: These encrypt your email purely on your and your recipient'due south computers (so chosen zero knowledge encryption).
2. Packaged Add-ins: These add together-ins are offered equally role of a bundle that additionally includes a client portal or file sharing service.

Encyro has an advantage compared to standalone add together-ins (zero knowledge encryption) that, with Encyro, your sent and received messages are
available exterior of the Outlook add-in as well. For instance, if y'all happen to be away from your PC with the Outlook and the add-in installed, then with Encyro, you could access your secure letters via a mobile device or a web login from another computer by visiting encyro.com. For the stand up-alone add together-ins just the add-in installed with your Outlook application has the ability to decrypt your secure messages.

Encyro also has an advantage over packaged add together-ins in terms of cost. The Encyro Outlook Addin is bachelor gratuitous while most all packaged add-ins require a paid subscription to their complete product. If you only need the Outlook encryption characteristic, then you can use Encyro for free.

A more detailed discussion of Outlook encryption add together-in features is provided in this commodity.

Determination

We described iii methods to encrypt e-mail in Outlook: using certificates (S/Mime), Office 365 Message Encryption (OME), and using encryption add together-ins. Among the three methods, the option to use add-ins is the lowest cost, and also allows using any electronic mail business relationship every bit sender and for receivers. It is the easiest to apply in most scenarios except for cases such every bit communicating with a government agency or large enterprise that has already opted to setup email encryption certificates (in which instance Method 1 is required).

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Source: https://blog.encyro.com/how-to-encrypt-email-in-outlook/

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