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Cloudron Forum

Apps | Demo | Docs | Install
  1. Cloudron Forum
  2. FreeScout
  3. Cannot connect with TSL/SSL

Cannot connect with TSL/SSL

Scheduled Pinned Locked Moved Solved FreeScout
32 Posts 9 Posters 5.8k Views 9 Watching
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  • T TestDesk

    Good day @all

    I hope you are well. I am happy to be with you and to work with you on solutions and feedbacks.

    Currently, I have the following problem, short summary:

    • FreeScout installed and mailbox set up - works.
    • Checked email settings (system) with a test email - works
    • Mailbox set up for incoming email - works

    Now the problem:
    Sending an e-mail via the mailbox (SMTP) does not work.

    The following error message appears:

    Expected response code 220 but got code "500", with message "500 Unrecognised command"
    

    Bildschirmfoto 2021-03-06 um 10.40.50.png

    I have checked the settings for SMTP several times. With the same settings I was able to set up Thunderbrid without any problems.

    I took my settings from the official description, see screenshot.

    SMTP settings

    What I noticed:
    As soon as I set the encryption from TLS to NONE, the sending works.

    Is it a BUG or have I overlooked something?

    Thanks in advance for your help.

    girishG Offline
    girishG Offline
    girish
    Staff
    wrote on last edited by
    #13

    @testdesk Setting encryption to NONE is correct setting when FreeScout is installed on the same server as Cloudron mail. When FreeScout is installed in another server, then you have to use TLS.

    The reason is a bit esoteric. Internally, Cloudron uses containers and the mail container is called 'mail'. Many apps don't work properly if you try to connect with the hostname as 'mail' but the TLS certificate says 'my.domain.com' (because of hostname mismatch). So, for historic reasons, we do not enable TLS for connection within the server itself. In this case, FreeScout is in same server as mail server and thus TLS option is not available. This is totally safe because the full connection is within the server. If you move your freescout to another server, then remember to put it to TLS.

    1 Reply Last reply
    0
    • girishG Offline
      girishG Offline
      girish
      Staff
      wrote on last edited by
      #14

      I have put a doc note here - https://docs.cloudron.io/apps/freescout/#cloudron-mailbox

      ianhyzyI 1 Reply Last reply
      1
      • girishG girish

        I have put a doc note here - https://docs.cloudron.io/apps/freescout/#cloudron-mailbox

        ianhyzyI Offline
        ianhyzyI Offline
        ianhyzy
        wrote on last edited by
        #15

        @girish I've copied the info from the screenshot here (Freescout and cloudron are on the same machine; mailgun is configured as the outbound SMTP provider in Cloudron settings; there are two mail-enabled domains) but I'm getting an error about the port being closed:

        e5e07995-31b8-4b48-bf1a-9e2159442304-image.png
        87ee3de7-b9e4-41e3-a916-a799d2414df2-image.png

        Could this be my firewall/ISP or did I misconfigure something?

        micmcM girishG 2 Replies Last reply
        0
        • ianhyzyI ianhyzy

          @girish I've copied the info from the screenshot here (Freescout and cloudron are on the same machine; mailgun is configured as the outbound SMTP provider in Cloudron settings; there are two mail-enabled domains) but I'm getting an error about the port being closed:

          e5e07995-31b8-4b48-bf1a-9e2159442304-image.png
          87ee3de7-b9e4-41e3-a916-a799d2414df2-image.png

          Could this be my firewall/ISP or did I misconfigure something?

          micmcM Offline
          micmcM Offline
          micmc
          wrote on last edited by
          #16

          @ianhyzy Try PORT 2525 with TLS/SSL encryption 😉

          Andy

          Ignorance is not an excuse anymore!
          https://AutomateKit.com

          ianhyzyI 1 Reply Last reply
          0
          • micmcM micmc

            @ianhyzy Try PORT 2525 with TLS/SSL encryption 😉

            Andy

            ianhyzyI Offline
            ianhyzyI Offline
            ianhyzy
            wrote on last edited by
            #17

            @micmc Got the same port blocked error with that:

            617a032e-deae-4253-9605-0190f339352f-image.png

            micmcM 1 Reply Last reply
            0
            • ianhyzyI ianhyzy

              @micmc Got the same port blocked error with that:

              617a032e-deae-4253-9605-0190f339352f-image.png

              micmcM Offline
              micmcM Offline
              micmc
              wrote on last edited by
              #18

              @ianhyzy Try NO encryption?

              Ignorance is not an excuse anymore!
              https://AutomateKit.com

              ianhyzyI 1 Reply Last reply
              0
              • micmcM micmc

                @ianhyzy Try NO encryption?

                ianhyzyI Offline
                ianhyzyI Offline
                ianhyzy
                wrote on last edited by
                #19

                @micmc same error 😞

                micmcM 1 Reply Last reply
                0
                • ianhyzyI ianhyzy

                  @micmc same error 😞

                  micmcM Offline
                  micmcM Offline
                  micmc
                  wrote on last edited by
                  #20

                  @ianhyzy I'm guessing your 'mail' mx is the cloudron one and that ALL email settings are enabled and GREEN for the domain you use for your FreshScout?

                  Ignorance is not an excuse anymore!
                  https://AutomateKit.com

                  ianhyzyI 1 Reply Last reply
                  0
                  • micmcM micmc

                    @ianhyzy I'm guessing your 'mail' mx is the cloudron one and that ALL email settings are enabled and GREEN for the domain you use for your FreshScout?

                    ianhyzyI Offline
                    ianhyzyI Offline
                    ianhyzy
                    wrote on last edited by
                    #21

                    @micmc Yup, green light and works with other apps

                    micmcM 1 Reply Last reply
                    0
                    • ianhyzyI ianhyzy

                      @micmc Yup, green light and works with other apps

                      micmcM Offline
                      micmcM Offline
                      micmc
                      wrote on last edited by
                      #22

                      @ianhyzy I meant the status like this for the specific domain
                      alt text

                      Ignorance is not an excuse anymore!
                      https://AutomateKit.com

                      ianhyzyI 1 Reply Last reply
                      0
                      • micmcM micmc

                        @ianhyzy I meant the status like this for the specific domain
                        alt text

                        ianhyzyI Offline
                        ianhyzyI Offline
                        ianhyzy
                        wrote on last edited by
                        #23

                        @micmc yup, all good:

                        2364a80b-2404-430f-9c45-3b837e95a8b9-image.png

                        micmcM 1 Reply Last reply
                        0
                        • ianhyzyI ianhyzy

                          @girish I've copied the info from the screenshot here (Freescout and cloudron are on the same machine; mailgun is configured as the outbound SMTP provider in Cloudron settings; there are two mail-enabled domains) but I'm getting an error about the port being closed:

                          e5e07995-31b8-4b48-bf1a-9e2159442304-image.png
                          87ee3de7-b9e4-41e3-a916-a799d2414df2-image.png

                          Could this be my firewall/ISP or did I misconfigure something?

                          girishG Offline
                          girishG Offline
                          girish
                          Staff
                          wrote on last edited by
                          #24

                          @ianhyzy said in Cannot connect with TSL/SSL:

                          Could this be my firewall/ISP or did I misconfigure something?

                          Yes, most likely. Is port 587 open in your firewall ? Also, if this server is at home, do you have loopback NAT working on your router?

                          ianhyzyI micmcM 3 Replies Last reply
                          0
                          • ianhyzyI ianhyzy

                            @micmc yup, all good:

                            2364a80b-2404-430f-9c45-3b837e95a8b9-image.png

                            micmcM Offline
                            micmcM Offline
                            micmc
                            wrote on last edited by
                            #25

                            @ianhyzy Your SMTP outbound is set as RELAY not as DIRECT this is something I was wondering because normally Cloudron should sety this automatically at installation time if your SMTP status is set. It seems to me that it might means you've set an outbound SMTP service on this domain and you now try to use the direct settings.

                            Ignorance is not an excuse anymore!
                            https://AutomateKit.com

                            ianhyzyI 1 Reply Last reply
                            0
                            • micmcM micmc

                              @ianhyzy Your SMTP outbound is set as RELAY not as DIRECT this is something I was wondering because normally Cloudron should sety this automatically at installation time if your SMTP status is set. It seems to me that it might means you've set an outbound SMTP service on this domain and you now try to use the direct settings.

                              ianhyzyI Offline
                              ianhyzyI Offline
                              ianhyzy
                              wrote on last edited by ianhyzy
                              #26

                              @micmc yeah I have mailgun set as the outbound SMTP server, but I get similar errors when I try to use mailgun directly. I would screenshot the error but it's a stack trace that takes up the whole screen

                              micmcM 1 Reply Last reply
                              0
                              • girishG girish

                                @ianhyzy said in Cannot connect with TSL/SSL:

                                Could this be my firewall/ISP or did I misconfigure something?

                                Yes, most likely. Is port 587 open in your firewall ? Also, if this server is at home, do you have loopback NAT working on your router?

                                ianhyzyI Offline
                                ianhyzyI Offline
                                ianhyzy
                                wrote on last edited by
                                #27

                                @girish I have 587 port forwarded and no, I need to look into NAT loopback

                                1 Reply Last reply
                                0
                                • ianhyzyI ianhyzy

                                  @micmc yeah I have mailgun set as the outbound SMTP server, but I get similar errors when I try to use mailgun directly. I would screenshot the error but it's a stack trace that takes up the whole screen

                                  micmcM Offline
                                  micmcM Offline
                                  micmc
                                  wrote on last edited by
                                  #28

                                  @ianhyzy Yeah, that's what I thought. Try to use default SMTP (no mailgun) on the domain and then use the same settings on the app. OR the contrary on both as well. The same SMTP for the domain and the app.

                                  Ignorance is not an excuse anymore!
                                  https://AutomateKit.com

                                  1 Reply Last reply
                                  0
                                  • girishG girish

                                    @ianhyzy said in Cannot connect with TSL/SSL:

                                    Could this be my firewall/ISP or did I misconfigure something?

                                    Yes, most likely. Is port 587 open in your firewall ? Also, if this server is at home, do you have loopback NAT working on your router?

                                    ianhyzyI Offline
                                    ianhyzyI Offline
                                    ianhyzy
                                    wrote on last edited by
                                    #29

                                    @girish I use a Unifi UDM-PRO at home and from what I can tell hairpin / NAT Loopback is enabled by default, and I don't recall ever disabling it

                                    ianhyzyI 1 Reply Last reply
                                    0
                                    • girishG girish

                                      @ianhyzy said in Cannot connect with TSL/SSL:

                                      Could this be my firewall/ISP or did I misconfigure something?

                                      Yes, most likely. Is port 587 open in your firewall ? Also, if this server is at home, do you have loopback NAT working on your router?

                                      micmcM Offline
                                      micmcM Offline
                                      micmc
                                      wrote on last edited by
                                      #30

                                      @girish He'd set mailgun as his default SMTP relay on the outbound mail for the domain, but apparently the app installed with default SMTP assumption?

                                      Will apps install with the SMTP relay set on domain's outbound mail, or it will they still assume the default settings, even if a relay is set before apps installation?

                                      Ignorance is not an excuse anymore!
                                      https://AutomateKit.com

                                      1 Reply Last reply
                                      0
                                      • ianhyzyI ianhyzy

                                        @girish I use a Unifi UDM-PRO at home and from what I can tell hairpin / NAT Loopback is enabled by default, and I don't recall ever disabling it

                                        ianhyzyI Offline
                                        ianhyzyI Offline
                                        ianhyzy
                                        wrote on last edited by
                                        #31

                                        @ianhyzy of course I tried Mailgun again and it seems to have worked - I must have had something off earlier. It seems to be taking the inbox a little longer than I thought to receive messages but they are coming in.

                                        ianhyzyI 1 Reply Last reply
                                        0
                                        • ianhyzyI ianhyzy

                                          @ianhyzy of course I tried Mailgun again and it seems to have worked - I must have had something off earlier. It seems to be taking the inbox a little longer than I thought to receive messages but they are coming in.

                                          ianhyzyI Offline
                                          ianhyzyI Offline
                                          ianhyzy
                                          wrote on last edited by
                                          #32

                                          @ianhyzy so it looks like I spoke too soon- the test email came in, but the email I sent from my Gmail account never appeared

                                          1 Reply Last reply
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