Reset Email not sending

[matthias-at-merona]

Hi all,
sorry if this is a duplicate, but I could not find similar issues.

First: Great product you built. I deployed it on a Hetzner server in a Docker Coolify environment and after initial struggles it works really well.

However, I noticed that password reset mails do not arrive. All I can find in the logs is "error: [sendEmail] Connection timeout" for the ssl configuration. I tried email configurations according to your password reset docs both with a throwaway google mail account and with a dedicated Strato smtp email address. Tried tls and ssl with respective ports 587 and 465 according to their documentation. The tls configuration specifically works for other services, only librechat runs into issues.

Do you have an idea what the problem could be? Is the timeout just kind of a catch-all error message, or a specific indication on a misconfiguration I can follow? Is the issue that it runs inside of Docker and that I need additional wiring? If so, are there variables I can set inside .env that let me do this, or would I need scripts to handle any of that?

My .env email configuration (in case of obvious issues here already) is

EMAIL_ALLOW_SELFSIGNED=false
EMAIL_ENCRYPTION=tls
EMAIL_ENCRYPTION_HOSTNAME=
EMAIL_FROM=some@mail
EMAIL_FROM_NAME=somename
EMAIL_HOST=smtp.strato.de
EMAIL_PASSWORD=somelongandsecurepassword
EMAIL_PORT=587
EMAIL_SERVICE=
EMAIL_USERNAME=some@mail

Thanks for reading and thanks in advance 😄

Edit:
Actually, for my tls configuration I receive the error error: [sendEmail] E8D16D12967A0000:error:0A00010B:SSL routines:ssl3_get_record:wrong version number:../deps/openssl/openssl/ssl/record/ssl3_record.c:354: which is at least different to a timeout.

Edit 2:
I don't think this has anything to do with the issue here but just for future readers who are stuck in a similar way:
After googling the above error I tried starttls (which is not a protocol, I know, and which is not supported by Strato) and tried various ports, all of which only resulted in error: [sendEmail] Invalid login: 535 5.7.8 Authentication failed: wrong user/password.

[danny-avila]

Sorry that you're struggling here. it could be that the port is not being correctly interpreted as an integer, I will try that and see if it works for you with your original settings.

[matthias-at-merona]

Your interface looks way different than mine.

When I was talking about the Domains for API field, I meant this one:

Your step by step guide has some specifics that are unique to my situation, like the Coolify version. I would advise changing those. Also, I would not put port 3080 onto the Firewall OK list. It has no business being exposed to the rest of the internet, let your proxy rewire that. Only access user oriented web pages over 80 (http) and 443 (https), and then configure it so that 80 redirects to 443.

You can set that in Coolify Project Configuration > Advanced. I at least have a Force Https field I can check.

[ctwhome]

that is funny because my version is only two more than yours

[matthias-at-merona]

I noticed than in new services I set up I am missing the General and Advanced Tabs is well. Those are important, why would they take them out?

[matthias-at-merona]

@danny-avila Figured it out.
Apparently 587 cannot handle TLS on server connection sometimes? Usually people get around this by setting the nodemailer secure flag to false, which means initial communication to server is not encrypted. I did some trial and error experimentation, and apparently setting the librechat EMAIL_ENCRYPTION variable to nothing instead of TLS or whatnot achieves this behaviour. As a workaround this works for now. I am not sure about the implications here. Did I generally give up encryption? Does it use some default? How does this work if my server insists on encrypted communication?
Having an env variable for this while keeping the encryption as TLS might be nice. If the communication is still encrypted and this only affects the initial handshake then leave it like this I'd say.

[matthias-at-merona]

@ctwhome
In the meantime I also figured out why my interface looks different from yours.

docker compose import from the libre chat docker compose into a probably new coolify project.

This was not true. When initially creating the project resource, do not create anything Docker based. Do Git based, select Public Repository. This gives you a much wider array of options to configure your application. Sorry for the mixup.

[rafae2k]

@matthias-at-merona can you share your docker compose deploy of librechat?

[matthias-at-merona]

@rafae2k Nothing fancy if you mean the automatically generated Docker Compose file. It mostly takes the librechat compose and adds labels and network stuff. Looks like this:

services:
  api:
    container_name: api-<containername>-bunchanumbers
    ports:
      - '${PORT}:${PORT}'
    depends_on:
      - mongodb
      - rag_api
    image: 'ghcr.io/danny-avila/librechat-dev:latest'
    restart: always
    user: '${UID}:${GID}'
    extra_hosts:
      - 'host.docker.internal:host-gateway'
    environment:
      - HOST=0.0.0.0
      - 'MONGO_URI=mongodb://mongodb:27017/LibreChat'
      - 'MEILI_HOST=http://meilisearch:7700'
      - 'RAG_PORT=${RAG_PORT:-8000}'
      - 'RAG_API_URL=http://rag_api:${RAG_PORT:-8000}'
    volumes:
      - '/data/coolify/applications/<containername>/.env:/app/.env'
      - '/data/coolify/applications/<containername>/images:/app/client/public/images'
      - '/data/coolify/applications/<containername>/logs:/app/api/logs'
    networks:
      <containername>: null
    labels:
      - whole lot of auto generated traefik and caddy stuff, just let coolify do its thing
      - in here will also be the info you set using the "Domains for API (i)" field. Set that.
  mongodb:
    container_name: mongodb-<containername>-bunchanumbers
    image: mongo
    restart: always
    user: '${UID}:${GID}'
    volumes:
      - '/data/coolify/applications/<containername>/data-node:/data/db'
    command: 'mongod --noauth'
    networks:
      <containername>: null
    labels:
      - coolify.managed=true
      - coolify.version=4.0.0-beta.360
      - coolify.applicationId=4
      - coolify.type=application
      - coolify.name=mongodb-<containername>-bunchanumbers
      - coolify.pullRequestId=0
  meilisearch:
    container_name: meilisearch-<containername>-bunchanumbers
    image: 'getmeili/meilisearch:v1.7.3'
    restart: always
    user: '${UID}:${GID}'
    environment:
      - 'MEILI_HOST=http://meilisearch:7700'
      - MEILI_NO_ANALYTICS=true
    volumes:
      - '/data/coolify/applications/<containername>/meili_data_v1.7:/meili_data'
    networks:
      <containername>: null
    labels:
      - coolify.managed=true
      - coolify.version=4.0.0-beta.360
      - coolify.applicationId=4
      - coolify.type=application
      - coolify.name=meilisearch-<containername>-bunchanumbers
      - coolify.pullRequestId=0
  vectordb:
    container_name: vectordb-<containername>-bunchanumbers
    image: 'ankane/pgvector:latest'
    environment:
      POSTGRES_DB: <somedatabase>
      POSTGRES_USER: <someuser>
      POSTGRES_PASSWORD: <somepassword>
    restart: always
    volumes:
      - 'pgdata2:/var/lib/postgresql/data'
    networks:
      <containername>: null
    labels:
      - coolify.managed=true
      - coolify.version=4.0.0-beta.360
      - coolify.applicationId=4
      - coolify.type=application
      - coolify.name=vectordb-<containername>-bunchanumbers
      - coolify.pullRequestId=0
  rag_api:
    container_name: rag_api-<containername>-bunchanumbers
    image: 'ghcr.io/danny-avila/librechat-rag-api-dev-lite:latest'
    environment:
      - DB_HOST=vectordb
      - 'RAG_PORT=${RAG_PORT:-8000}'
    restart: always
    depends_on:
      - vectordb
    env_file:
      - .env
    networks:
      <containername>: null
    labels:
      - coolify.managed=true
      - coolify.version=4.0.0-beta.360
      - coolify.applicationId=4
      - coolify.type=application
      - coolify.name=rag_api-<containername>-bunchanumbers
      - coolify.pullRequestId=0
volumes:
  pgdata2:
    name: pgdata2
networks:
  <containername>:
    name: <containername>
    external: true
configs: {  }
secrets: {  }