Netgate Discussion Forum
    • Categories
    • Recent
    • Tags
    • Popular
    • Users
    • Search
    • Register
    • Login

    outlook not downloading folders

    Scheduled Pinned Locked Moved General pfSense Questions
    20 Posts 6 Posters 1.5k Views 6 Watching
    Loading More Posts
    • Oldest to Newest
    • Newest to Oldest
    • Most Votes
    Reply
    • Reply as topic
    Log in to reply
    This topic has been deleted. Only users with topic management privileges can see it.
    • C Offline
      calvin.quint
      last edited by

      I am using my personal outlook.com email on Outlook 2019 behind pfsense and Outlook does not download the mail inside the folders?

      NollipfSenseN 1 Reply Last reply Reply Quote 0
      • NollipfSenseN Offline
        NollipfSense @calvin.quint
        last edited by

        @calvin-quint Did you forget to login?

        pfSense+ 23.09 Lenovo Thinkcentre M93P SFF Quadcore i7 dual Raid-ZFS 128GB-SSD 32GB-RAM PCI-Intel i350-t4 NIC, -Intel QAT 8950.
        pfSense+ 23.09 VM-Proxmox, Dell Precision Xeon-W2155 Nvme 500GB-ZFS 128GB-RAM PCIe-Intel i350-t4, Intel QAT-8950, P-cloud.

        C 1 Reply Last reply Reply Quote 0
        • C Offline
          calvin.quint @NollipfSense
          last edited by

          @nollipfsense it downloads mail just not my folders.

          1 Reply Last reply Reply Quote 0
          • stephenw10S Offline
            stephenw10 Netgate Administrator
            last edited by

            That is not pfSense dircetly. It must be something about the connection Outlook doesn't like.

            Are you routing traffic over a VPN?

            Steve

            N 1 Reply Last reply Reply Quote 0
            • N Offline
              netblues @stephenw10
              last edited by

              It could be mtu, but I would also suspect corrupted local psd.

              C 1 Reply Last reply Reply Quote 0
              • C Offline
                calvin.quint @netblues
                last edited by

                @netblues This is not a VPN connection.

                N 1 Reply Last reply Reply Quote 0
                • N Offline
                  netblues @calvin.quint
                  last edited by

                  @calvin-quint Can you eg try tethering via a mobile phone and see if it works bypassing pf?

                  C 1 Reply Last reply Reply Quote 0
                  • C Offline
                    calvin.quint @netblues
                    last edited by

                    @netblues I am on a desktop I am using Cat 6 no wireless card.

                    johnpozJ 1 Reply Last reply Reply Quote 0
                    • johnpozJ Offline
                      johnpoz LAYER 8 Global Moderator @calvin.quint
                      last edited by

                      If your client is behind pfsense, and your email server is behind pfsense. How would pfsense have anything to do with the conversation at all?

                      Are you doing some sort of nat reflection, or haproxy your bouncing off of on pfsense?

                      An intelligent man is sometimes forced to be drunk to spend time with his fools
                      If you get confused: Listen to the Music Play
                      Please don't Chat/PM me for help, unless mod related
                      SG-4860 24.11 | Lab VMs 2.8, 24.11

                      C 1 Reply Last reply Reply Quote 0
                      • C Offline
                        calvin.quint @johnpoz
                        last edited by

                        @johnpoz There is no email server behind pfsense. I am using the Microsoft outlook.com email service. Outlook is not downloading my emails in my folders. It downloads my inbox not in folders.

                        johnpozJ 1 Reply Last reply Reply Quote 0
                        • johnpozJ Offline
                          johnpoz LAYER 8 Global Moderator @calvin.quint
                          last edited by johnpoz

                          How would pfsense have anything to do with that? Your conversation would be inside a https tunnel. What you do inside that tunnel pfsense doesn't care nor have any clue.

                          If whatever your doing required you to go to some other fqdn, that might have a problem with dns? Or a connection problem even to some other IP..

                          I don't use outlook, my wife has a hotmail account ;) So not something I could prob test anything with.. Oh wait I do have a live.com account - but don't really use it. Is there something I could test? Could you show exactly what is not working, so I could try and duplicate?

                          But just to your inbox vs folders seems like rules thing on outlook, I really don't see how that could have anything to do with pfsense.. But if you could show example be happy to try and duplicate.

                          An intelligent man is sometimes forced to be drunk to spend time with his fools
                          If you get confused: Listen to the Music Play
                          Please don't Chat/PM me for help, unless mod related
                          SG-4860 24.11 | Lab VMs 2.8, 24.11

                          1 Reply Last reply Reply Quote 0
                          • stephenw10S Offline
                            stephenw10 Netgate Administrator
                            last edited by

                            I have seen some weird issues with MTU problems where some sites appear to be working except some feature. But only over VPN, I've never seen that with a straight routed https connection.

                            Steve

                            johnpozJ 1 Reply Last reply Reply Quote 0
                            • johnpozJ Offline
                              johnpoz LAYER 8 Global Moderator @stephenw10
                              last edited by

                              I am not really understanding what is not working even. Are you using imap? When you talk about stuff downloading to folders? Are you talking about saving an attachment in an email?

                              Are these folders in your mailbox on outlook? Some folder on your PC makes no sense to me to be honest..

                              Please show example of what is not working, and would be happy to duplicate and look to what could be the problem. If possible..

                              An intelligent man is sometimes forced to be drunk to spend time with his fools
                              If you get confused: Listen to the Music Play
                              Please don't Chat/PM me for help, unless mod related
                              SG-4860 24.11 | Lab VMs 2.8, 24.11

                              C N 2 Replies Last reply Reply Quote 0
                              • C Offline
                                calvin.quint @johnpoz
                                last edited by

                                @johnpoz I am using the default mail setting for the outlook.com mail provider.

                                86ab1e75-9b57-4d99-bff3-a8b034b6666e-image.png

                                The folders I am refering to is if you create a rule to sort your incoming from a certain sender.

                                1 Reply Last reply Reply Quote 0
                                • N Offline
                                  netblues @johnpoz
                                  last edited by

                                  @johnpoz This is outlook service hosted and offered by Microsoft.
                                  Its a standard web mail over https

                                  If the op is using the local outlook client, then it is again ssl encrypted traffic. Nothing fancy here, network wise

                                  As for the issue, if you are using the web client and encounter the issue, then its a microsoft problem.
                                  Try creating a new folder, and move something in there
                                  Does it work?

                                  johnpozJ 1 Reply Last reply Reply Quote 0
                                  • johnpozJ Offline
                                    johnpoz LAYER 8 Global Moderator @netblues
                                    last edited by johnpoz

                                    Even if using the local outlook client.. Its a outlook thing - this has NOTHING to do with pfsense..

                                    Sorting mail into folders would have zero to do with pfsense..

                                    https://www.lifewire.com/auto-filter-sender-mail-to-folder-outlook-1173804

                                    When you create rules in outlook the client on your desktop, when talking to exchange these rules can run on the server, or they can run on the client.. Recheck your rules you have setup for filtering traffic into folders. But there is no way pfsense has anything to do with that not working.

                                    here I created a rule on outlook.com

                                    rule.png

                                    That rule that moves email from that address to testfolder has zero to do with pfsense, and there is no possible way pfsense could have anything to do with that working or not working.

                                    Here I just sent test message for my rule - and it ends up in my testfolder.

                                    folderrule.png

                                    An intelligent man is sometimes forced to be drunk to spend time with his fools
                                    If you get confused: Listen to the Music Play
                                    Please don't Chat/PM me for help, unless mod related
                                    SG-4860 24.11 | Lab VMs 2.8, 24.11

                                    1 Reply Last reply Reply Quote 0
                                    • stephenw10S Offline
                                      stephenw10 Netgate Administrator
                                      last edited by

                                      Exactly, pfSense does not filter that.

                                      The fact it appears to only happen when behind pfSense could be Windows set to not pull that data when on that network. I could imagine it set to not think that network is limited data and hence not pull the full folder listing. Guessing there but Windows can see it's on a different network and can apply different action if told to do so.

                                      Steve

                                      johnpozJ 1 Reply Last reply Reply Quote 0
                                      • johnpozJ Offline
                                        johnpoz LAYER 8 Global Moderator @stephenw10
                                        last edited by

                                        Still not really understanding the exact issue.

                                        Are rules not working, or are you using local outlook client setup for imap, and not showing you your folders in the local client?

                                        You may need to requery for your imap folders..

                                        So exact info of what is the problem would be helpful in helping you.. Other than your using outlook ;)

                                        An intelligent man is sometimes forced to be drunk to spend time with his fools
                                        If you get confused: Listen to the Music Play
                                        Please don't Chat/PM me for help, unless mod related
                                        SG-4860 24.11 | Lab VMs 2.8, 24.11

                                        S NollipfSenseN 2 Replies Last reply Reply Quote 0
                                        • S Offline
                                          SteveITS Rebel Alliance @johnpoz
                                          last edited by

                                          @johnpoz He's saying new messages aren't showing in various folders. Presumably they show if he logs in to the web site (?) or some other device. Agreed it'd be pretty difficult to pin on pfSense.

                                          @calvin-quint Outlook.com should be using an Exchange type of account as I recall, so would have created a .OST file to cache recent mail. Although one can scan a .OST file for errors like a .PST file it is usually far easier and faster to just close Outlook, rename/delete the .OST file, and let Outlook redownload the data into a new file that it will create. That's generally the first thing I do when troubleshooting any sort of Outlook data issue when .OST files are involved.

                                          Only install packages for your version, or risk breaking it. Select your branch in System/Update/Update Settings.
                                          When upgrading, allow 10-15 minutes to reboot, or more depending on packages, and device or disk speed.
                                          Upvote 👍 helpful posts!

                                          1 Reply Last reply Reply Quote 0
                                          • NollipfSenseN Offline
                                            NollipfSense @johnpoz
                                            last edited by NollipfSense

                                            @johnpoz said in outlook not downloading folders:

                                            Still not really understanding the exact issue.

                                            That's why I asked OP whether OP forgot to login! It appears not a pfSense issue.

                                            pfSense+ 23.09 Lenovo Thinkcentre M93P SFF Quadcore i7 dual Raid-ZFS 128GB-SSD 32GB-RAM PCI-Intel i350-t4 NIC, -Intel QAT 8950.
                                            pfSense+ 23.09 VM-Proxmox, Dell Precision Xeon-W2155 Nvme 500GB-ZFS 128GB-RAM PCIe-Intel i350-t4, Intel QAT-8950, P-cloud.

                                            1 Reply Last reply Reply Quote 0
                                            • First post
                                              Last post
                                            Copyright 2025 Rubicon Communications LLC (Netgate). All rights reserved.