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I've tried everything from this post that applied as well as the answers from this post.

I can connect successfully with Kodi on Android as well as NetDrive on Windows.

I cannot connect with Kodi on Windows or by trying to map the drive to a letter or add a network location on Windows.

Path formulas I've tried:

  • https://blah.domain.net:custom_port
  • https://blah.domain.net:custom_port/share
  • \\blah.domain.net:custom_port@SSL\share
  • \\blah.domain.net@SSL:custom_port\share

I am very much in need of a free and or native mapping approach. From what I gather this may not be possible natively due to a crippled/bugged Windows authentication issue.

I am only concerned with Windows 7+.

I also ran through this:

You have to install your self-signed certificate first. Run Internet Explorer with administrative rights (UAC won’t work!):

  • Enter your WebDAV URL
  • Click on Continue to this website (not recommended)
  • Click on Certificate Error in the red colored address bar
  • Click on View certificates
  • In the Certificate dialog, press Install Certificate
  • In the Certificate Import Wizard, click Next
  • On page 2 of the wizard, select Place all certificates in the following store and click Browse;
  • In the Select Certificate Store dialog, select Trusted Root Certification Authorities, click OK
  • In the wizard, click Next, click Finish
  • If a security message pops up, choose Yes
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2 Answers 2

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Your issue seems to be that you use self-signed certificates, which require to somehow install your own root certificate to make it trusted by Windows. And that's the buggy part in Windows.

Instead, it is simpler to circumvent this by installing "already trusted" LetsEncrypt certificates on your Synology WebDAV device – at least with the current software "Disk Station Manager" (DSM) 6.2.1, but probably also earlier versions.

Here's a process how to use your Synology WebDAV device using custom Dynamic DNS (DDNS) and LetsEncrypt certificates. You could choose from any of the standard DDNS providers in the DSM interface, but the solution here is cheaper: just the cost of the domain itself.

  1. Register an account at a DNS hoster that provides Dynamic DNS for free, add a domain to that account, and enable Dynamic DNS for one of its subdomains.

    For example, this is possible with dd24.com as follows. You create DDNS subcomains for your domain under "Domains → My Domains → [select domain] → DynamicDNS".

  2. Use these instructions by Synology (in section "Setting Up a Customized DDNS Provider") to configure your DDNS domain for your WebDAV device. In the case of d24.com. the correct DDNS update URL format to enter would be one of these two (following documentation by dd24.com and the Synology help page linked above):

    https://dynamicdns.key-systems.net/update.php?hostname=__HOSTNAME__&password=__PASSWORD__&ip=auto
https://dynamicdns.key-systems.net/update.php?hostname=__HOSTNAME__&password=__PASSWORD__&ip=__MYIP__

  3. Use these instructions by Synology (in section "Certificates from Let's Encrypt") to configure your WebDAV enabled device with LetsEncrypt certificates that are automatically updated every 90 days. These certificates will be served for WebDAV access for sure, because it uses the same port as HTTPS (i.e. 443).

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  • I've personally lost all interest and need for WebDAV so I can't test or mark as accepted. I've upvoted and if someone else can vouch for this as a viable solution, I'll mark as accepted.
    – Enigma
    Dec 7, 2018 at 16:46
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Not really the answer I was looking for and I would still like to find a real answer but for the time being I am mapping an SFTP share using the free SFTP Net Drive tool by Eldos which works well enough and should be about as secure as WebDAV HTTPS would be.

Update:

SFTP was also a rather dysfunctional solution.

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