Problem connecting to server via SFTP (SSH) with FileZilla on macOS (Monterey)

[backslash]

I am trying to connect via SFTP to my server (Debian based NAS) using FileZilla 3.63.1 and it works perfectly fine with one exception:

As soon as I try to connect via FileZilla and replace the external IP "XXX.XXX.XXX.XX" that I got assigned from my ISP and which gets renewed every 24 hours with my dynamic DNS URL like "xyz.myfritz.net" then the connection does not work anymore through FileZilla:

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Status: Connecting to xyz.myfritz.net...
Response: fzSftp started, protocol_version=11
Command: open "johndoe@xyz.myfritz.net" 22
Error: Connection timed out after 20 seconds of inactivity
Error: Could not connect to server
Status: Waiting to retry...

By using the external IP "XXX.XXX.XXX.XX" from the router it works with FileZilla as it should:

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Status: Connecting to XXX.XXX.XXX.XX...
Status: Using username "johndoe".
Status: Connected to XXX.XXX.XXX.XX
Status: Retrieving directory listing...
Status: Listing directory /srv/dev-disk-by-uuid-xyz/Home/johndoe
Status: Directory listing of "/srv/dev-disk-by-uuid-xyz/Home/johndoe" successful

If i try to connect from my Mac terminal being it SSH/SFTP using the very same xyz.myfritz.net dynamic DNS URL everything works as expected.

Using the Windows version of FileZilla within the same network environment works also as expected.

A regular "oldschool" non SSH FTP connection works perfect using FileZilla for macOS in combination with the very same dynamic xyz.myfritz.net URL.

The only combination that does not work is a SFTP connection with FileZilla for macOS and the dynamic xyz.myfritz.net URL.

Is this a FileZilla for Mac and/or macOS issue?

[botg]

Open a Terminal and check the output of these two commands:

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ping xyz.myfritz.net
ping6 xyz.myfritz.net

Each should either result in a hostname resolution failure, or if they resolve to an actual address, be pingable.

[backslash]

Open a Terminal and check the output of these two commands:

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ping xyz.myfritz.net
ping6 xyz.myfritz.net

Each should either result in a hostname resolution failure, or if they resolve to an actual address, be pingable.

Both are being resolved and the respective addresses are both pingable from the terminal

[botg]

Can you connect to both these addresses with ssh if you explicitly enter them instead of the hostname?

[backslash]

Can you connect to both these addresses with ssh if you explicitly enter them instead of the hostname?

I can't! I can ssh the IPv4 address but not the IPv6. So is this a misconfiguration of the server or does the dynamic DNS service not properly reflect the IPv6 address?

[boco]

Unfortunately, it could be either one. Using ifconfig in a terminal session on the server NAS will reveal the actual IPv6 IPs assigned (use alternative ways to gather assigned IPs if there's no terminal). Does the global address (not LLA nor ULA/SLA) match with what the DNS names resolve into?

[backslash]

Does the global address (not LLA nor ULA/SLA) match with what the DNS names resolve into?

No it does not. I think we narrowed down the issue. At least it is not a FileZilla issue then.

[GB_Informatics]

Hello,

I have set up OpenVPN between my Synology server with OpenVPN configured on it. With Filezilla on macos I can't connect via nas.synology.me. with Cyberbuck it works.
The problem arises when I'm connected using connection sharing on my mobile phone.
Can someone please help me?