1 Topic by mrimichael

  • mrimichael
  • Member
  • Offline
  • Registered: 2017-01-05
  • Posts: 30

Topic: iPhone email cannot connect to SMTP

==== REQUIRED BASIC INFO OF YOUR IREDMAIL SERVER ====
- iRedMail version (check /etc/iredmail-release): 1.1 PGSQL edition
- Deployed with iRedMail Easy or the downloadable installer? Downloadable installer
- Linux/BSD distribution name and version: Ubuntu 18.04.4 LTS
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): PGSQL
- Web server (Apache or Nginx): Nginx
- Manage mail accounts with iRedAdmin-Pro? Yes
- [IMPORTANT] Related original log or error message is required if you're experiencing an issue.
====

IOS version 13.4, updated on 1 April. I have never tried to connect this phone to iRedMail before.

Good day,

I can use my iPhone's email app to check other mail, like my hostmonster domain account, without any problem.

I can also download POP3 mail with my iPhone from my iRedMail server. I cannot connect to the SMTP server. Regardless of what I try the iPhone tells me "The SMTP server doesn't support Password authentication. Please check your account settings and try again.

It gives me similar messages for the other authentications:

MD5 Challenge-Response
NTLM
HTTP MD5 Digest

I've tried them all on both ports 25 and 587 and using SSL and not using SSL.

At the moment, I can use MS OutLook 2010 to connect and send email without any problem.

How do I fix this?

Thanks,

Michael

----

Spider Email Archiver: On-Premises, lightweight email archiving software developed by iRedMail team. Supports Amazon S3 compatible storage and custom branding.

2 Reply by PaulCahill

  • PaulCahill
  • PaulCahill
  • Member
  • Offline
  • From: Northern KY, USA
  • Registered: 2018-06-02
  • Posts: 49

Re: iPhone email cannot connect to SMTP

Are you using a self-signed cert for the encryption? 587 and SSL should work I believe, with your username and password for authentication. I haven't loaded a cert onto mine yet, so I can't test (Just installed).

PaulCahill's Website

3 Reply by ms2504 (edited by ms2504 2020-04-04 15:08:19)

  • ms2504
  • Member
  • Offline
  • Registered: 2019-06-15
  • Posts: 70

Re: iPhone email cannot connect to SMTP

Same problem for me.

SMTP port 25 will not work for sure, because is not enabled for sending mail.

SMTP port 587 is enabled for TLS, not for SSL.

I am using LetsEncrypt certificate, and it works very well, I don't think it is a certificate issue.

I changed the configuration following this document https://docs.iredmail.org/enable.smtps.html  to use SMTP port 465 with SSL, and it works for older mail clients I still need to support.  And it works on old Outlook clients.

But in iPhone configuration, also setting SMTP port 465 with SSL enabled, connection is refused, as all other authentication options (MD5 - NTLM - HTTP MD5 Digest).

I don't know what to do.

4 Reply by mrimichael

  • mrimichael
  • Member
  • Offline
  • Registered: 2017-01-05
  • Posts: 30

Re: iPhone email cannot connect to SMTP

I’m using a certificate I bought from digicert. It’s weird. I can receive mail via pop3

My POP settings are:
Use SSL
Password authentication
Server port 110

SMTP settings are
Use SSL
Password authentication
Server port 25. I’ve tried 587 and 465. None work

I’ve tried with and without password authentication but nothing works.

In addition, I have a similar problem with Outlook 2010. I’ve used the same settings as with IOS but it won’t even log on to POP. What am I doing wrong?


mrimichael wrote:

==== REQUIRED BASIC INFO OF YOUR IREDMAIL SERVER ====
- iRedMail version (check /etc/iredmail-release): 1.1 PGSQL edition
- Deployed with iRedMail Easy or the downloadable installer? Downloadable installer
- Linux/BSD distribution name and version: Ubuntu 18.04.4 LTS
- Store mail accounts in which backend (LDAP/MySQL/PGSQL): PGSQL
- Web server (Apache or Nginx): Nginx
- Manage mail accounts with iRedAdmin-Pro? Yes
- [IMPORTANT] Related original log or error message is required if you're experiencing an issue.
====

IOS version 13.4, updated on 1 April. I have never tried to connect this phone to iRedMail before.

Good day,

I can use my iPhone's email app to check other mail, like my hostmonster domain account, without any problem.

I can also download POP3 mail with my iPhone from my iRedMail server. I cannot connect to the SMTP server. Regardless of what I try the iPhone tells me "The SMTP server doesn't support Password authentication. Please check your account settings and try again.

It gives me similar messages for the other authentications:

MD5 Challenge-Response
NTLM
HTTP MD5 Digest

I've tried them all on both ports 25 and 587 and using SSL and not using SSL.

At the moment, I can use MS OutLook 2010 to connect and send email without any problem.

How do I fix this?

Thanks,

Michael

5 Reply by ZhangHuangbin

  • ZhangHuangbin
  • ZhangHuangbin
  • iRedMail Developers
  • Offline
  • Registered: 2009-05-06
  • Posts: 31,088

Re: iPhone email cannot connect to SMTP

Dear all,

For MUA configuration, please follow our tutorial: https://docs.iredmail.org/#mua

With default iRedMail settings, port 25 is not used for end user to send email, so you should not configure MUA to use it at all, use port 587 with TLS (or STARTTLS) instead.

Old MUA may not support 587 with TLS/STARTTLS, you can consider enabling port 465 with SSL for them: https://docs.iredmail.org/enable.smtps.html

6 Reply by ZhangHuangbin

  • ZhangHuangbin
  • ZhangHuangbin
  • iRedMail Developers
  • Offline
  • Registered: 2009-05-06
  • Posts: 31,088

Re: iPhone email cannot connect to SMTP

Also, grab a free SSL cert if you don't have a valid ssl cert yet: https://docs.iredmail.org/letsencrypt.html
It's easy and free.