S Mime Outlook Web App Mac Rating: 6,1/10 5302 reviews

Aug 26, 2014 To work around this issue, close Internet Explorer 11, reopen the page in compatibility mode, and then the S/MIME option will work as expected. When you use this workaround, Internet Explorer 11 saves your Compatibility View settings for the website. Every time that you access the Outlook Web App site, Compatibility View will be used. Jun 25, 2019  However, a major problem existed for users of S/MIME: you HAD to use your desktop client to view your encrypted emails and validate any signed emails. Users could not view their S/MIME emails on a browser via Outlook Web App (OWA). They also couldn’t view their S/MIME emails on their smartphones via the Outlook mobile app. If that's all I do, and we sign back in to the account and go to the Mail settings, the S/MIME section says we need to add outlook.office365.com to the allowed domains in the extension. If we do that and restart Chrome, the S/MIME section disappears. Remove the domain and restart, and it's back. Jun 08, 2020  Configure S/MIME settings in Exchange Online for Outlook on the web. 6/8/2020; 2 minutes to read +2; In this article. As an admin for Exchange Online, you can set up Outlook on the web (formerly known as Outlook Web App) to allow sending and receiving S/MIME-protected messages.

Enterprise Webmail link:

In the Under Secretary of the Army memorandum regarding Enterprise Email, the @mail.mil email address is the default email address on all new CACs issued since 6 January 2014.

NOTE:

Between mid October 2019 and mid February 2020 everyone in the Army was migrated to PIV AUTH certificate for Email access. You no longer select the Email certificate for Enterprise Email. If you see the below message after selecting your Email certificate, there is a good chance your account has been changed to using the Authentication certificate. So, please try your Authentication certificate instead of the Email certificate.

Mac users who choose to upgrade to Mac OS Catalina (10.15.x) will need to uninstall all 3rd Party CAC enablers per https://militarycac.com/macuninstall.htm

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Created a 'retiring' page dedicated to providing information for people getting ready to retire. People need to understand they will no longer have access to DoD Enterprise Email and AKO once they surrender their CAC or date of retirement (whichever happens first).

Receiving something similar to below image stating 'The DNS server might be having problems. Error Code: INET_E_RESOURCE_NOT_FOUND'

Follow guidance here to change your DNS server.

Accessing https://web.mail.mil requires the steps below and an email account already created

Windows Installation Steps
Step 1: Obtain a CAC Reader
Step 2:CAC Reader driver
Step 3:DoD Certificates
Step 4:ActivClient
Step 4a:Update ActivClient
Step 5:IE adjustments
Step 6:Select the Authentication certificate when prompted

Windows 10 users will see the certificate selection differently than older versions of Windows. Click More choices to see additional certificates. Select the correct one, and then click OK. NOTE: Dual Persona users will need to ActivID 7.1.0.153 to view your PIV certificate.


Mac Users - Some of the information below will not work for you. Start here for Mac specific instructions. If Mac user is dual persona / PIV AUTH, please look here to learn how to figure out which certificate is your actual PIV certificate.

Problem 1:How can I check my DoD Enterprise Email other thanOWA when I'm not in the office?

INFORMATION: The DoD Enterprise Email does NOT have the ability to be accessed using Outlook or other email program on a computer that is not on the .mil or .gov network. Read the 3 lines with double dashes. This means it cannot be set it up on a personal computer using Outlook.

Solution 1-1: Yes, you can forward it but, only to another .mil or .gov email address. (For all mail.mil users)

Solution 1-2: Yes, use your government owned BlackBerry, iPhone, iPad, or Android device (Only for Business Class users)

Solution 1-3: Yes, bring your government computer with you and use VPN (For all mail.mil users, normally only business class users)

Solution 1-4: If your organization uses Citrix, you may be able to use it to login with your CAC enabled home computer and access your Outlook via the Citrix client. (Only for Business Class users)

Solution 1-5: You can check your email via an iPhone or iPad using OWA or Android using a mobile CAC reader and middleware. (For all mail.mil users)

Problem 2: Youreceive the following error message when attempting to access https://web.mail.mil

Solution 2:You don't have an Enterprise Email account yet. Check back with your organization to find out the approximate date it will be created.All Army users will have their account created automatically within 24 hours of receiving your CAC. You can call the Army Enterprise Service Desk-Worldwide at 866-335-2769 to find out who your Entitlement Manager is for your command if you've had your CAC longer than 48 hours.

Problem 3:Your Email has transitioned to Enterprise Email and your information is incorrect in the Global Address List (GAL).

Solution 3-1: Picture guide created for US Army Reserve Soldiers, but will work for everyone

Solution 3-2: If your rank is wrong in the GAL (examples: 1SG vs. MSG, SPC vs. CPL vs. SP4, or SGM vs. CSM), you have to visit an ID card office to get it corrected.

Problem 4:Receive 'HTTP/1.1 503 Service Unavailable' when attempting to access your email via OWA.

Information: This is caused when the Exchange server is down, or having problems.

Solution 4:Try accessing your email at a later time

Problem 5:How do I add my PIV cert to my CAC, so, I can access my email?

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Solution 5: Follow guidance on PIV page

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Problem 6: My calendar and times are off in my OWA calendar

NOTE: It is possible when you initially set up your OWA access you selected the defaults, which included the time zone set to Zulu time.

Solution 6: Click Options, See All Options.., Settings, Regional. Change Current Time Zone to your location in the world. Remember to click Save (lower right corner of screen)

Problem 7:I Can't view Encrypted emails in OWA / web.mail.mil(currently or prior to receiving a new CAC).

Solution 7-1: Make sure you have the S/MIME control installed.

REMINDER: This is only available in Internet Explorer (32 bit). It will NOT work with the 64 bit version of Internet Explorer, Edge, Chrome, Firefox, or on Macs.

Information: Browsers other than 32 bit Internet Explorer are not capable of using S/MIME in OWA, this is because it is an Active-X control. By design web browsers other than 32 bit Internet Explorer do not support Active-X (and Browser Helper Objects).

An OPTION is to use DISA's Secure Access File Exchange (SAFE) (https://safe.apps.mil) if you are waiting for orders or something that has PII in it. Your unit can upload it to SAFE and you will receive a link to download the file(s) you need.

NOTE: Internet Explorer 11 runs in 32 bit mode by default, so, this should not be an issue. You would have had to have selected 'Enable 64-bit processes for Enhanced Protected Mode' to run in 64 bit mode. More information can be read here.

Here's how to install s/mime: Click Options, See All Options.., Settings, S/MIME, click on download the S/MIME control

NOTE2: If you don't see these options, your settings may have you in 'Use the blind and low vision' mode. To verify, Select Options, Accessibility. If your screen looks like the image below, uncheck the box next to Use the blind and low vision experience. Select Save (diskette above big word accessibility), Sign out, log back into your webmail, and follow instructions above.

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NOTE3: If you have problems installing the S/MIME control, make sure ActiveX Filtering in the Tools, Safety menu is unchecked, then attempt to download again.

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Solution 7-2: Make sure you have your @mail.mil address on your CAC. Here's how to change / update your email address on your CAC. The process is practically identical to what you see on the PIV page.

Solution 7-3: If you have recently received a new CAC, follow this guide to recover your former CAC certificate(s), NOTE: you MUST be on the military UnClassified network to access the certificate recovery websites, which means you cannot access the links from your home computer.

Solution 7-4: If you are receiving a blank screen after logging into OWA, please follow this guide

Problem 8:How do I get support for my Enterprise Email account?

Solution 8-1 (when at Home or Work): Contact the Army Enterprise Service Desk - Worldwide by calling: 866-335-2769 24x7or go to: https://aesd-w.army.mil

Solution 8-1a (Army Reserve): Contact the Army Reserve Help desk at: 844-770-3737, or [from your Army Reserve computer] go to: https://esahelp

Problem 9: How do I turn off conversation view inweb.mail.mil?
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Solution 9: Click View, uncheckUse Conversations.

Problem 10: I am over my storage limit, and I can't send any email. How can I increase my email storage capacity? DEE only gives me 512 MB, what can I do?


Solution 10: Call 866-335-2769 and ask who your Entitlement Manager is for your branch of service and command. Then email them to ask to be converted to a Business Class account. NOTE: The AESD may be able to upgrade you depending on who you work for.

S Mime Outlook Web App Mac Os

Problem 11:How can I find out how much mailbox space I'm using in OWA?

Solution 11:Hover your mouse over your name, a bubble similar to this should pop up and show you. NOTE: This only works on Windows computers

Problem 12:Receive message: 'This message can't be decrypted. If you have a smart card-based digital ID, insert the card and try to open the message again' when using OWA

Solution 12:Make sure the email address on your CAC is also in your Exchange profile. NOTE: This is why Army users have @mail.mil email address on their CAC. You can update your email address by following this guidance.

Problem 13:I have PCSd to a new installation / location. How do I update my information in the Mail.mil Global Address List? NOTE: when you change your Installation, this will silently move your mail account to a closer DECC to your new duty station. You can see a list of them here.

Solution 13: Look at Solution 3-1 above

Problem 14:How do I configure my DoD Enterprise Email when at my Government computer using Outlook? NOTE: NOT available from home computer, OWA is only option

Solution 14:Follow this guide

Problem 15:You can get to https://web.mail.mil with your CAC and PIN. The next screen shows your actual mail server https://web-XXXX.mail.mil/owa however, this link only timeouts. It also times out if you go straight to it.

Solution 15:Follow this guide

Problem 16:I live in Korea (or another foreign country) and am unable to access Mail.mil from my personal computer. What can I do? Also helps problems accessing DoD sites from the USA when receiving messages regarding DNS.

Solution 16-1: Try changing your DNS server IPs and see it this works for you.

Here's How in Windows to manually configure the DNS settings.

1. Right click on your Wireless / Ethernet connection (down by your clock)

2. Select Open Network and Sharing Center, or Open Network & Internet settings

3. Click Change Adapter Settings, or Change adapter options

4. Right Click on your active internet connection (example: Wi-Fi or Local Area Connection), select Properties

5. Under This connection uses the following items: scroll down and click on Internet Protocol Version 4 (TCP/IPv4), then click Properties

6. Select the option Use the following DNS server addresses:. This is where you manually configure your DNS servers:

NOTE: It is up to you if you want to use Quad 9 or Cloudflare. You might try each of them separately.

Quad 9 - enter 9.9.9.9 for Preferred DNS server, and leave alternate DNS server blank. Click OK, then click Close

or

Cloudflare - enter 1.1.1.1 for Preferred DNS server, and 1.0.0.1 for alternate DNS server. Click OK, then click Close

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If you are a Spectrum customer, you may need to change the DNS on your router, changing it on the client doesn't seem to allow access for some users like the ideas above.

Here's How on a Mac to manually configure the DNS settings.

1. Click Apple icon -> System Preferences, Network.

2. Select the network connection service you want to use (usually Wi-Fi or Ethernet, unless you named it something else) in the list, then click the Advanced (button).

3. Click the DNS (tab), click the (+) at the bottom of the DNS Servers list. This is where you will add DNS server IP addresses.

NOTE: It is up to you if you want to use Quad 9 or Cloudflare. You might try each of them separately.

Quad 9 - enter 9.9.9.9 and leave alternate DNS blank

or

Cloudflare - enter 1.1.1.1 for first line and 1.0.0.1 the second line

4. When you're finished, click OK, then close the open window

If you are a Spectrum customer, you may need to change the DNS on your router, changing it on the client doesn't seem to allow access for some users like the ideas above.

Solution 16-2:Overseas personnel may need to try a VPN solution

Solution 16-3:Contact the Army Enterprise Service Desk to let them know you are having problems.

Problem 17:You are trying to updateMilConnect [are married to another Service member] and cannot get your information to show you as the Sponsor. You are probably showing up as a family member.

Solution 17: Follow guide in problem 3-1 above

Problem 18: I can't access my web.mail.mil email server, is the website down?

S Mime Outlook Web App Mac

Solution 18: Visit: https://status.mail.mil (use your Email or PIV cert) you may be able to find out information about the status of your DECC.

Problem 19: Why am I being prompted for my PIN constantly when using Windows 10, 8 / 8.1, 7 built in smart card utility, or with ActivClient 7.0.1.x and 7.0.2.x?

Solution 19: Windows 10, 8 / 8.1 built in smart card utility. DoD Enterprise Email may ask you constantly for your PIN. The only solution I've found is for you to install ActivID 7.1.0.153

Problem 20: Firefox refuses to cooperate with Mail.mil

Solution 20: Follow installation guidance on Firefox page. I followed #1, #2, & #3.

Problem 21: See 'The ActiveX control needs to be enabled in Internet Explorer for Outlook Web App to work correctly. Click here to sign out, enable the ActiveX control, and then sign in to Outlook Web App.'

Solution 21:Follow this entire guide.

Problem 22: See: 'Your S/MIME control is out of date.'

Solution 22: Follow Solution above (Since the instructions they give you here are missing a step).

NOTE: This will only work with Internet Explorer (32 bit), NOT the 64 bit version (or on a Mac or any other web browser)

Problem 23: Receive 'Error Code: 500 Internal Server Error. The server denied the specified Uniform Resource Locator (URL). Contact the server administrator.'

Solution 23 (Windows users):Follow this information

Solution 23 (Mac users): Follow these ideas

Problem 24: The 'New' button does not work to create a New email (on Windows 8.1)

Solution 24: The problem is incompatible Browser Mode and Document Mode. In order for IE 11 on Windows 8.1 to work with the EE-OWA, the Browser Mode can be any from IE11 (regular or Compatibility Mode) to IE7 and the Document Mode MUST be IE8 Standards or higher (e.g. IE9 Standards). Access that Menu by pressing F12. A small window will open at the bottom of the browser. The options are on the right of the Menu Bar of that small window.

Problem 25: I am receiving the error message: 'No digital ID for signing has been found. If you have a smart card-based digital ID, insert the card and try to send the message again. You can also try sending the message without a digital signature.'

Information: This affects users who have their AKO email address on one or both military and civilian CACs.

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Solution 25-1: Update / change email address on your CAC(s) to your Enterprise Email address.

Outlook Web App Enable Smime

Solution 25-2:Visit an ID card office to have them update your email address on your CAC(s) to your DoD Enterprise Email address.

Solution 25-3:Your computer still has your certificates from your former CAC, and is trying to use them instead of your new CAC certificates. Follow slide 23 in this guide to clear them.

Problem 26: Web.mail.mil / OWA locks up when trying to delete a thread of email, moving messages, and dismissing reminders.

NOTE: You may have received an update to Skype on your Windows computer. This update comes with Skype Click to Call (C2C). People have noticed the issue appear and also noticed phone numbers in emails suddenly appeared in blue (hyperlinks) with a Skype symbol next to them.

Solution 26: Uninstall C2C and the issue with locking up OWA when deleting email threads, moving messages, and dismissing reminders will go away.

Problem 27: When forwarding emails from web.mail.mil, the attachments are not showing in the message, but somehow the recipient is still getting the attachment.

Solution 27: The attachment is hidden from your current view. Follow guidance in Problem 28)

Problem 28: I cannot see my attachments once I add them to a new email message in OWA when using Internet Explorer 11? How do I know they are actually there before I send the email?

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Solution 28-1: Add the attachment to the email you are creating. Save the email as a draft. Close the email message, reopen it. You should now see that the attachment is in the outgoing email.

Solution 28-2: Use Google Chrome when sending attachments. Please know you will not be able to encrypt email when using Chrome.

Solution 28-3: Make sure you have Silverlight installed (http://www.microsoft.com/getsilverlight)

Solution 28-4: Follow this guide when using Internet Explorer

Problem 29: Receiving a message stating: There were problems validating this signature. (More information) when trying to read encrypted or signed emails in OWA

When you click on More information, you get this

Solution 29:Add https://*.mail.mil to your web browser's Trusted Sites (I know this goes against other guidance on this website).

Here's how: Open Internet Explorer, Tools, Internet Options, Security (tab), Trusted Sites (green checkmark), Sites (button), Copy https://*.mail.mil and paste it into the Add this website to the zone: (box), select Add, then close to get out of Trusted Sites.

Other branches of the military should follow this guide

Problem 30: What do the 3 letters mean after your name and before the @ sign?

Example: first.m.last.mil@mail.mil

Information 30:

Information 30a:

A PIV is comprised of your 10 digit DoD ID # followed by 6 more digits

The 1st digit is the Organizational Category

1 = Federal Government Agency

2 = State Government Agency

3 = Commercial Enterprise

4 = Foreign Government

Source: Paragraph 5.1.5.2.8 https://www.dmdc.osd.mil/smartcard/docs/DoD%20PIV%20Transitional%20Implementation%20Guide.pdf

The 2nd through 5th are the Agency Code

2100 = Department of the Army

5700 = Department of the Air Force

1700 = Department of the Navy

1727 = Department of the Navy - US Marine Corps

9700 = Department of Defense - Other Agencies

7008 = US Coast Guard

7520 = US Public Health Service

1330 = National Oceanic and Atmospheric Administration

Source: Paragraph 5.1.5.2.1 https://www.dmdc.osd.mil/smartcard/docs/DoD%20PIV%20Transitional%20Implementation%20Guide.pdf

The 6th position is the Person / Organization Association Category

1 = Employee, example: NAF (Non Appropriated Funds)

2 = Civil, example: CIV / LN (Civilian / Local National)

3 = Executive Staff

4 = Uniformed Service, example: MIL (Military)

5 = Contractor CTR (Contractor)

6 = Organization Affiliate, example: NFG / Volunteer / Foreign Military (Non-Federal Government)

7 = Organization Beneficiary

Source: Paragraph 5.1.5.2.10 https://www.dmdc.osd.mil/smartcard/docs/DoD%20PIV%20Transitional%20Implementation%20Guide.pdf

Problem 31: After receiving a new CAC, you receive the following message when trying to use your CAC. 'A smart card was detected but is not the one required for the current operation. The smart card you are using may be missing required driver software or a required certificate.'

Solution 31: Your computer still has your certificates from your former CAC, and is trying to use them instead of your new CAC certificates. Follow slide 23 in this guide to clear them.

Problem 32: Receive the following error message 'Your current security settings do not allow this file to be downloaded.'

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Solution 32: Open Internet Explorer, click Tools, Internet Options, Security (tab), select the Internet icon, click the Custom level.. (button), scroll down to the section titled Downloads and under File download make sure Enable is selected.

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Problem 33: I can't access my webmail

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Solution 33:Try disabling your Antivirus / web protection, if this works. you may need to find a compatible AV program. Sometimes this may still not work, where an actual uninstall is all that will work.

Avast users do this: Add *mail.mil* [and any other websites you can't access] to the Exclusions section of Main Settings, see image. More information about what Avast is doing can be read here.

AVG users follow their guidance by adding https://*.mail.mil to the exceptions list

Bitdefender users may need to uninstall the program and find a different Antivirus program

Kaspersky users follow their guidance by adding https://*.mail.mil to the exceptions list. Another person had to turn off the Parental controls.

-Another fix for Kaspersky users is to turn off 'Traffic Processing' under 'Network Settings'

McAfee users follow their guidance

Problem 34: Receiving 'This message contains an attachment encoded in a format that Outlook Web App doesn't recognize. Some of the information it contains may not be displayed in the message body.' when trying to open an attachment in an email using webmail.
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Solution 34: The attachment could be corrupt. Have them resend to you, they may also need to be send it unencrypted.

Problem 35:
Mac users are unable to add attachments to emails

Solution 35: Close OWA, download and install Microsoft Silverlight from: https://www.microsoft.com/getsilverlight once installed, log back into OWA and attach your file to your email.

Problem 36: You are a member of a Non Persona Entity (NPE) mailbox and need to access it via web.mail.mil

Click on your name

Start typing the name of the mailbox, you'll see it start to populate

Problem 37: Receive error message 'One or more errors occurred while the message was being sent. Error: (0x80004003)' with Lync or Skype installed when trying to send emails in OWA.

Solution 37: In Internet Explorer, click Tools, Manage Add-ons. Find and select Lync Browser Helper, click the Disable button

Problem 38: Receive error message 'This message can't be decrypted because its encryption algorithm isn't supported or your digital ID can't be found. If you have a smart card-based digital ID, insert the card and try again to open the message.'

or the same message followed by:

'The digital signature of this message couldn't be validated because an error occurred while the message was being loaded.'

Information 38: This error can be caused by the certificate in the Global Address List does not match what is on your CAC. Commonly caused with new cards issued within 24-48 hours.

Solution 38 (OWA users) part 1: Login to the Global Directory Service (GDS) at: https://dod411.gds.disa.mil/index.html (CAC required link (ID Certificate)),

Enter your last name and first name, click Search.

Click your underlined last name,

Select Download Certificate(s) as .cer file (Non-Outlook Users).

Save the file to your computer.

Double click the .cer file to view the valid from and todates.

Now open your IE web browser, navigate to Tools, Internet Options, Content (tab), Certificates (button), Personal (tab),

Select either of your Email certificates and select View (button), if these dates do not match the other file, then the GAL has the wrong certificate for you.

Solution 38 (OWA users) part 2: Follow guidance on PIV activation page to set up your Windows computer for the site. Then follow these instructions except DO NOT add a PCC to your CAC, if you do, you can try this idea, if it doesn't' work, you'll need to get a new CAC to undue it. Click in email address block, and don't change it, but select the button for changing it. After roughly 30 hours, your certificate will publish to the GAL and the errors should go away.

Solution 38 (Outlook users on Government computer): Publish your certificates to the GAL using Outlook, here's how:

-Outlook 2016, 2013, & 2010: File (tab), Options, Trust Center, Trust Center Settings..(button), E-mail Security, Click on Publish to GAL..(button)

-Outlook 2007: Tools, Trust Center.., E-mail Security, Click on Publish to GAL..(button)

Problem 39: While using OWA, you receive the following error message: 'The window couldn't be opened because pop-ups are current blocked by the browser. Would you like to open the window anyway? To avoid seeing this message in the future, turn off pop-up blocking in the settings for your browser.'

Solution 39: Uncheck 'Enable 64-bit processes for Enhanced Protected Mode*'

Here's where to find it: Open Internet Explorer, click Tools, Internet Options, Advanced (tab), scroll down to the the Security section.

Problem 40: Receive error message 'This message can't be sent in an encrypted form because your computer doesn't work with the required encryption methods. To send the message, remove encryption. If the problem continues, contact your helpdesk.' or 'One or more errors occurred while the message was being sent. Error: (0x80040154)'

Solution 40-1: If you have MalWare Bytes (MB) installed, it is blocking the VBScript from allowing you to send an email via OWA. You can right click it and close the program to see if this is what is causing your issue. If that doesn't work, try Solution 40-2 below.

Solution 40-2: Open Settings, Protection (tab), Advanced Settings (button), Under the Application Hardening (tab), Uncheck Disable Internet Explorer VB Scripting (under the Browsers heading), click Apply

Question: What exactly is 'Dual Persona?'

Answer: The easiest way to explain is to give you an example: an Army Reserve [or National Guard] Soldier who is also a DoD civilian [or contractor] and is authorized [or required] to have / carry / use two separate CACs. We are finding that people who were previously a contractor [or civilian] during the past three years [even if they left the job a year ago] are still classified as a Dual Persona in the eyes of DMDC and DISA.

Individuals that fall into this category HAVE to activate their PIV cert to be able to access their email on the DoD Enterprise Email.