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  • Outlook for Android will not connect

    Home Forums AskWoody support Non-Windows operating systems Android Outlook for Android will not connect

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      • #2353829
        AskWoody Plus

        Note sure if this is the right forum? Anyway, the problem is Outlook for Android.

        Some colleagues have access to their Exchange (on-premisse) account using Outlook on their smartphone. To allow this, I have port 443 open on the firewall. A simple but not very secure method, as the ProxyLogon leak showed. I DO have locked down access to only allow Dutch IP-adressess. But anyhow, I want something more secure, like VPN. So I set up a VPN configuration on the firewall to allow access to port 443 on the Exchange server. And to be able to access that server by name, I also allowed access to port 53 on a local DNS server. Installed VPN client on a smartphone running Android and when the VPN is enabled, I can use a webbrowser to access OWA on the Exchange server by it’s local name, like

        With this working, it should be easy to change the Outlook settings on the phone with the new server address. And there the fun begins. You cannot change account settings like server address, login name, password etc. in Outlook. No way. Out of the question. It took me a while to realize it can’t be done. Surely I was doing something wrong, since the ability to change those settings is pretty basic. But not for the people of Microsoft. Right.

        So in Outlook on the phone, delete account, create new account. Fill in the exact same settings of the old account, but for the server address changed it from to Outlooks responds Login error. The connection to your mail server timed out. Please check your mail settings. The last sentence is a good one; when you tap OK, you don’t get back to the account settings, no, you’re sent back to the Choose account type page. And start all over again. Without any luck.

        So I remove the Outlook app, restarted the phone, installed it again, tried again configuring without success, deleted the Outlook data, restarted the phone, tried again …. etc. No result. Message is the same every time. Then I tried the Gmail app. Created a new account using the exact same account settings I had tried with Outlook and… works without any issue.

        My conclusion:

        • There’s no problem on the server side
        • There’s no problem with the VPN
        • There’s no problem with the phone
        • There’s no problem with the Gmail app.
        • There IS a problem with the Outlook app.

        Now I don’t care having to use the Gmail app instead of Outlook, but my colleagues DO. They want Outlook on their phone. So how do I tackle this problem? If at all?

      • #2356221
        AskWoody Plus

        Sadly no answers to this question 🙁

        I’ve been digging further and Microsoft happens to have issued an article about the error message: “The connection to your mail server timed out” error in Outlook for iOS or Outlook for Android – Exchange | Microsoft Docs

        It’s caused by the wrong TLS-version. So I checked it with the Remote Connectivity Analyzer and TLS turns out fine. It did however, have a problem with the certificate. I’ve been using free certificates of for years and without any problems. But the Connectivity Analyzer cannot verify the certificate chain, since CACert is not on the list of trusted root certificate authorities. To rule out any certificate problems, I bought a new wild card certificate and installed it. No more complaints of the Connectivity Analyzer, but allas, I still cannot create an Outlook account to access the Exchange server over VPN…

        Any ideas? Plz?

      • #2356229
        AskWoody Lounger

        We use excahnge server too. Most of our phones run iOS, but several have Android too.

        The mail via exchange account works on both Android an iOS.

        The advantage of iOS is, that alle those telephones have the same environment.

        Nearly on every Android phone, there seems to be different version of operating system and and also Outlook. Nevertheless I am able to set corporate email even on Android and Outlook app.
        My observation from your post is this:

        I still cannot create an Outlook account to access the Exchange server over VPN

        I do not set any VPN on any type of the telephone. I just enter these in Outlook app
        – select exchange
        – enter web address of the exchange server
        – enter domain
        – enter domain username (remember, that domain user should be different from email address!)
        – domain user password

        I dont need no VPN, just internet connection.

        Hard to tell, why you get timeout error, there could be some misconfiguration on the exchange, or simply the authentication is not done in required time (thus your username, domain or password are incorrect).

        Dell Latitude E6530, Intel Core i5 @ 2.6 GHz, 4GB RAM, W10 1809 Enterprise

        HAL3000, AMD Athlon 200GE @ 3,4 GHz, 8GB RAM, Fedora 29

        • #2356314
          AskWoody Plus

          Hi Doriel,

          Thing is, when an account for Outlook for Android (or iOS for that respect) is configured for the WAN side, it works fine. For the WAN side, this means the server name is DNS record at the ISP for this name points to our Exchange server. When I start the VPN on the phone, the only difference for the Outlook account is it accesses the Exchange server over the LAN and thus the server name should be it’s local name: Resolving this name is done on one of the local DNS servers. But then Outlook throws the time out.

          If I start a browser on the phone, I can access OWA over the LAN by just typing – works fine. So IMO there’s no problem with the VPN.

          Most annoying thing is trouble shooting. I’m not very familiar with smart phones, but there seems to be no logging of any kind. Comes to mind I could try capture network traffic on the firewall for the phone when it tries to connect, if at all. Dig into that this weekend…

          • This reply was modified 1 day, 3 hours ago by Simon_Weel.
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