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    S/MIME and Office 365

    Scheduled Pinned Locked Moved IT Discussion
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    • ObsolesceO
      Obsolesce @Kelly
      last edited by Obsolesce

      @Kelly Maybe the problem is your Global Address List (GAL), or you simply aren't waiting long enough.
      Let me try a run-through here:

      1. User joins the company.
      2. O365 email account is set up for new user.
      3. New user logs on to new Mac computer, sets up Outlook.
      4. IT Admin sends new user his/her certificate via email (or by whatever means). Preferably a .PFX so it contains private key and whole CA chain.
      5. New user or IT admin goes into new users Outlook trust center/email security settings to set signing/encryption certificate(s).
      6. While still in Outlook Email Security settings, "Publish to GAL" button is clicked, success confirmation pops up.
      7. After 24 hours, or via users manually updating their Address Book in Outlook, users are now able to send encrypted emails to new user.

      Basically, when you publish to GAL, it's loading all certificate information to O365. Every else's address books will automatically update I think the default is once per day. So if users can't send the new user encrypted emails, they either need to update their address book in Outlook, or simply wait a day or so. As long as they are all part of the same organization in Office 365, they'll share the GAL and get the same one.

      KellyK 1 Reply Last reply Reply Quote 0
      • KellyK
        Kelly @Obsolesce
        last edited by

        @Tim_G said in S/MIME and Office 365:

        @Kelly Maybe the problem is your Global Address List (GAL), or you simply aren't waiting long enough.
        Let me try a run-through here:

        1. User joins the company.
        2. O365 email account is set up for new user.
        3. New user logs on to new Mac computer, sets up Outlook.
        4. IT Admin sends new user his/her certificate via email (or by whatever means). Preferably a .PFX so it contains private key and whole CA chain.
        5. New user or IT admin goes into new users Outlook trust center/email security settings to set signing/encryption certificate(s).
        6. While still in Outlook Email Security settings, "Publish to GAL" button is clicked, success confirmation pops up.
        7. After 24 hours, or via users manually updating their Address Book in Outlook, users are now able to send encrypted emails to new user.

        Basically, when you publish to GAL, it's loading all certificate information to O365. Every else's address books will automatically update I think the default is once per day. So if users can't send the new user encrypted emails, they either need to update their address book in Outlook, or simply wait a day or so. As long as they are all part of the same organization in Office 365, they'll share the GAL and get the same one.

        No, we're not doing anything from 6 on. There is no "Publish to GAL" button in Outlook for Mac. This is why we're distributing the public keys manually.

        ObsolesceO 1 Reply Last reply Reply Quote 0
        • ObsolesceO
          Obsolesce @Kelly
          last edited by

          @Kelly said in S/MIME and Office 365:

          @Tim_G said in S/MIME and Office 365:

          @Kelly Maybe the problem is your Global Address List (GAL), or you simply aren't waiting long enough.
          Let me try a run-through here:

          1. User joins the company.
          2. O365 email account is set up for new user.
          3. New user logs on to new Mac computer, sets up Outlook.
          4. IT Admin sends new user his/her certificate via email (or by whatever means). Preferably a .PFX so it contains private key and whole CA chain.
          5. New user or IT admin goes into new users Outlook trust center/email security settings to set signing/encryption certificate(s).
          6. While still in Outlook Email Security settings, "Publish to GAL" button is clicked, success confirmation pops up.
          7. After 24 hours, or via users manually updating their Address Book in Outlook, users are now able to send encrypted emails to new user.

          Basically, when you publish to GAL, it's loading all certificate information to O365. Every else's address books will automatically update I think the default is once per day. So if users can't send the new user encrypted emails, they either need to update their address book in Outlook, or simply wait a day or so. As long as they are all part of the same organization in Office 365, they'll share the GAL and get the same one.

          No, we're not doing anything from 6 on. There is no "Publish to GAL" button in Outlook for Mac. This is why we're distributing the public keys manually.

          I did not know that. I'm not as familiar with Outlook on Macs. What percentage of users use Outlook on a Mac?
          When I get some more time, I'll take a look at some things and get back to you.

          1 Reply Last reply Reply Quote 0
          • DashrenderD
            Dashrender
            last edited by

            Could your mac users do a setup on a windows machine just to push this, then move to their mac?

            KellyK 1 Reply Last reply Reply Quote 0
            • KellyK
              Kelly @Dashrender
              last edited by

              @Dashrender said in S/MIME and Office 365:

              Could your mac users do a setup on a windows machine just to push this, then move to their mac?

              It is possible, but I'm trying to simplify the process... 🙂

              1 Reply Last reply Reply Quote 0
              • DashrenderD
                Dashrender
                last edited by

                I don't know certs in Exchange at all - so don't crusify me for asking.

                How are your certs created? a cert server on your local network? If yes, are they used for other domain level things? If no - does MS have any solution inside O365 that can create these certs and keep it all inside O365? I thought they had security stuff inside O365, but really know nothing about it.

                KellyK 1 Reply Last reply Reply Quote 0
                • KellyK
                  Kelly @Dashrender
                  last edited by

                  @Dashrender said in S/MIME and Office 365:

                  I don't know certs in Exchange at all - so don't crusify me for asking.

                  How are your certs created? a cert server on your local network? If yes, are they used for other domain level things? If no - does MS have any solution inside O365 that can create these certs and keep it all inside O365? I thought they had security stuff inside O365, but really know nothing about it.

                  They've been created using OpenSSL on a stand alone system. Due to regulatory requirements we cannot store private keys in O365, so even if those systems existed we couldn't make use of them.

                  DashrenderD 1 Reply Last reply Reply Quote 0
                  • DashrenderD
                    Dashrender @Kelly
                    last edited by

                    @Kelly said in S/MIME and Office 365:

                    @Dashrender said in S/MIME and Office 365:

                    I don't know certs in Exchange at all - so don't crusify me for asking.

                    How are your certs created? a cert server on your local network? If yes, are they used for other domain level things? If no - does MS have any solution inside O365 that can create these certs and keep it all inside O365? I thought they had security stuff inside O365, but really know nothing about it.

                    They've been created using OpenSSL on a stand alone system. Due to regulatory requirements we cannot store private keys in O365, so even if those systems existed we couldn't make use of them.

                    aww.. ok.

                    1 Reply Last reply Reply Quote 0
                    • JaredBuschJ
                      JaredBusch
                      last edited by JaredBusch

                      @Tim_G for your reference, here is what I see on my MacBook. I am not using Certificates.
                      0_1484612690622_upload-19c490ab-7407-422a-8c78-62df439f696a

                      0_1484612500463_upload-4fe48f92-d023-4bb0-93a2-2b7e60a39864

                      ObsolesceO 1 Reply Last reply Reply Quote 2
                      • ObsolesceO
                        Obsolesce @JaredBusch
                        last edited by

                        @JaredBusch Thank you

                        1 Reply Last reply Reply Quote 0
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