Web UI docker - email on port 465 failing: i/o timeout

Support
#1

I’m attempting to get emailing working but have been unsuccessful. I am using same config as I have in other working containers but the ‘test’ email always fails with error:

Failed to send the email: read tcp 172.x.x.x:37342->198.x.x.x:465: i/o timeout.

There are no errors in the docker logs. The smtp server I am using (as specified by my hosting provider, is server187.web-hosting.com:465. This works in other containers. Help!

EDIT: I’ve also tried setting the email_skip_verify: true flag, but still no luck, same error.

#2

It can be anything — connectivity issue, firewall, packet fragmentation and mismatched mtu,….

I would start with testing connectivity from within the container, to distinguish duplicacy issue from environment.

#3

It’s on the same docker network and same container configuration as other containers with working SMTP connections. Is there any documentation for this in regards to docker that might indicate anything different from standard configs? Any way to enable more verbose logging?

EDIT: I confirmed that I am able to both ping and telnet into the smtp server from within the duplicacy container. So that leads me to believe there is something wrong with duplicity or that I’m missing configuration somewhere.

EDIT 2: I’m not this matters but I notice that every time I test the connection and I get the error message, the container’s outgoing port changes (but always points at the SMTP server’s port 465.

#4

Hey, did you ever figure this out? Having the same issue on Unraid/Docker. Confirmed that the Duplicacy container can ping the SMTP host, and I use the same SMTP settings within another container on the same Docker network.

#5

I’m having the same issue as well. I’m a new Duplicacy user from the black friday sale. I initially setup email notifications for scheduled backups and it was working perfectly fine. I don’t know when/why, but in the last few weeks it stopped working.

I was originally successfully using my SMTP provider’s port 587 (STARTTLS). However, when I test those settings now, I get the following error:
Failed to send the email: 535 Incorrect authentication data

I tried switching to port 465 (TLS) and that now gives me the same I/O timeout error described here.
Failed to send the email: read tcp 172.x.x.x:38074->185.x.x.x:465: i/o timeout

As a workaround for now I’ve setup gotify for the individual backups, but would much prefer the summary email.

#6

I couldn’t get it figured out with email even after more troubleshooting - I ended up setting up an alert with changedetection.io to watch for status changes on my backup schedule page (Failed, Completed, etc) which works well enough. I’m using the Hotio version of Duplicacy FWIW.

#7

Any other ideas @saspus ? I was using the Unraid community app which leverages your container.

As a test, I switched to using docker compose so I could try the “mini” option and leverage the 1.7.2 web version to see if it worked better, but the results are the same as above on the 1.8.x release.

It was originally successfully using my paid SMTP provider’s port 587 (STARTTLS). However, when I test those settings now, I get the following error:
Failed to send the email: 535 Incorrect authentication data

I tried switching to port 465 (TLS) and that now gives me the same I/O timeout error described here.
Failed to send the email: read tcp 172.x.x.x:38074->185.x.x.x:465: i/o timeout

If I try to use gmail (smtp.gmail.com:465), I receive
Failed to send the email: EOF

As a workaround, I’m using gotify for the individual backup pass/fail status, but I don’t know how to get the cumulative summary that is available via email.

#8

How do you get changedetection to see a private page?

#9

Just use internal IP address, or have containers on same Docker network. I reference mine via Tailnet name like [tailnet]:port

#10

Is it a self hosted service? When I googled it looked external.

#11

Oh I see what you mean. Yeah, Changedetection has a paid service, and they also have a selfhosted Docker container with full features for free

#12

Hey guys,

Did anyone figure this one out? I’m a new Duplicacy user and having the same issue, I can’t connect to a 465 smtp account (works well on another docker in the same network).

#13

Does it work with Gmail on port 587?

#14

It actually did work for me with port 587 on gmail (after setting up a new app password for authentication). I would prefer not to use gmail, but I’m glad at least that works as an alternative to my usual mail provider.

Any thoughts why certain providers/ports aren’t working?

#15

It’s explained at the link above. The expected behavior on smtp ports is different.