Enable TLS v1.0

BS1

ntozier OK, I tried with pop, pop+ssl, imap, imap+SSL, both with the IP address and the URL and the reply is
Fetching Email via IMAP or POP

Can't open mailbox {tls://10.10.1.22:143/imap/novalidate-cert}INBOX: invalid remote specification.

BS1

Fetching Email via IMAP or POP

Can't open mailbox {tls://10.10.1.22:995/pop3/ssl/novalidate-cert}INBOX: invalid remote specification

KevinTheJedi

@BS1

Run:

$ openssl s_client -connect 10.10.1.22:143 -starttls imap -tls1

Post a picture of your mail settings so we can see what you are trying to enter as the protocol, etc.

Cheers.

BS1

C:\Program Files\OpenSSL-Win64\bin>openssl s_client -connect 10.10.1.22:143 -sta
rttls imap -tls1
CONNECTED(00000080)

write:errno=0

no peer certificate available

No client certificate CA names sent

SSL handshake has read 191 bytes and written 130 bytes

Verification: OK

New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
SSL-Session:
Protocol : TLSv1
Cipher : 0000
Session-ID:
Session-ID-ctx:
Master-Key:
PSK identity: None
PSK identity hint: None
SRP username: None
Start Time: 1564674905
Timeout : 7200 (sec)
Verify return code: 0 (ok)

Extended master secret: no

KevinTheJedi

@BS1

Port 143 is the unencrypted port for IMAP. If you would like to use 143 you must use the protocol of just IMAP (NOT IMAP + SSL).

Cheers.

BS1

ntozier

You would remove the tls:// from the url I think if your not using ssl.

BS1

It does not seem to matter. Any combination that I use fails, and there does not seem to be anything generating errors as to "why?"

KevinTheJedi

@BS1

Any combination that I use fails, and there does not seem to be anything generating errors as to "why?"

Because the errors are listed in your mailserver's connection/error logs..

Cheers.

BS1

OK, now i have to ask a dumb question. It is not producing errors in the server APPLog. Is the connection/error log somewhere else?

ntozier

In exchange I think those go into the event viewer. (it's been years since I have had to look at them, so you might have to google it)

Tenggay

Hi ntozier

I'm trying to send email via SMTP but cannot make it work. I tried the following ways:

Disabled the MFA for specific user
Enabled/ Enforced MFA to specific user and use APP PASSWORD Instead.

We cannot disable the security defaults for our organization since it will put us on risk, and conditional access needs a premium plan on Azure.

I was able to use gmali using the APP PASSWORD created on gmail, but on O365 I am getting an error.

Hope you can share some thoughts about it.

Thank you.

KevinTheJedi

@Tenggay

As the error states, you should contact your administrator and/or mail provider for further assistance. It appears you have some very specific rules/setup on your mailserver.

Cheers.