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Mail Server Sent to Gmail but to Spam Folder Not Inbox

12 replies
ra
rashad #2

this is checktls details ,

CheckTLS ConfidenceFactor for “seen-lami.com”: 110 of 114 (96%, 124 max)

MX Server Pref Answer Connect HELO TLS Cert Secure From MTASTS DANE Score
mail.seen-lami.com
[191.96.31.100:25] 10 OK
(61ms) OK
(290ms) OK
(177ms) OK
(62ms) FAIL OK
(887ms) OK
(226ms) not tested not tested 110.00
Average 100% 100% 100% 100% 0% 100% 100% 110

Scan down DETAIL output below for info on errors and warnings.

Now you can test MTA-STS for your domain too!

Checking seen-lami.com from www12-azure.checktls.com(V03.71.00) at 2023-07-28T12:00:21Z:

seconds lookup result
[000.000] DNS LOOKUPS
[000.001] SEARCHLIST 104.131.108.216,134.209.169.224,1.1.1.1,8.8.8.8,67.207.67.3
[000.013] MX (10) mail.seen-lami.com
[000.022] MX:A–>mail.seen-lami.com 191.96.31.100

seconds test stage and result
[000.000] Trying TLS on mail.seen-lami.com[191.96.31.100:25] (10)
[000.061] Server answered
[000.351] <‑‑ 220 localhost ESMTP Postfix
[000.351] We are allowed to connect
[000.351] ‑‑> EHLO www12-azure.checktls.com
[000.528] <‑‑ 250-localhost
250-PIPELINING
250-SIZE 30720000
250-ETRN
250-STARTTLS
250-AUTH PLAIN
250-AUTH=PLAIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250-DSN
250 CHUNKING
[000.528] We can use this server
[000.529] TLS is an option on this server
[000.529] ‑‑> STARTTLS
[000.590] <‑‑ 220 2.0.0 Ready to start TLS
[000.590] STARTTLS command works on this server
[000.726] Connection converted to SSL
SSLVersion in use: TLSv1_3
Cipher in use: TLS_AES_256_GCM_SHA384
Perfect Forward Secrecy: yes
Session Algorithm in use: Curve X25519 DHE(253 bits)
Certificate #1 of 4 (sent by MX): EXPIRED
Cert VALIDATION ERROR(S): certificate has expired
So email is encrypted but the recipient domain is not verified
Cert Hostname VERIFIED (mail.seen-lami.com = mail.seen-lami.com DNS:mail.seen-lami.com DNS:www.mail.seen-lami.com)
Not Valid Before: Feb 21 23:42:23 2023 GMT
Not Valid After: May 22 23:42:22 2023 GMT
subject: /CN=mail.seen-lami.com
issuer: /C=US/O=Let’s Encrypt/CN=R3
Certificate #2 of 4 (sent by MX):
Cert VALIDATED: ok
Not Valid Before: Sep 4 00:00:00 2020 GMT
Not Valid After: Sep 15 16:00:00 2025 GMT
subject: /C=US/O=Let’s Encrypt/CN=R3
issuer: /C=US/O=Internet Security Research Group/CN=ISRG Root X1
Certificate #3 of 4 (added from CA Root Store):
Cert VALIDATED: ok
Not Valid Before: Jun 4 11:04:38 2015 GMT
Not Valid After: Jun 4 11:04:38 2035 GMT
subject: /C=US/O=Internet Security Research Group/CN=ISRG Root X1
issuer: /C=US/O=Internet Security Research Group/CN=ISRG Root X1
Certificate #4 of 4 (sent by MX):
Cert VALIDATED:
Not Valid Before: Jan 20 19:14:03 2021 GMT
Not Valid After: Sep 30 18:14:03 2024 GMT
subject: /C=US/O=Internet Security Research Group/CN=ISRG Root X1
issuer: /O=Digital Signature Trust Co./CN=DST Root CA X3
[000.825] > EHLO www12-azure.checktls.com
[000.887] <
250-localhost
250-PIPELINING
250-SIZE 30720000
250-ETRN
250-AUTH PLAIN
250-AUTH=PLAIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250-DSN
250 CHUNKING
[000.887] TLS successfully started on this server
[000.887] > MAIL FROM:test@checktls.com
[001.113] <
250 2.1.0 Ok
[001.113] Sender is OK
[001.113] > QUIT
[001.177] <
221 2.0.0 Bye

ra
rashad #3

also i can receive from icloud email but when i tried to send to icloud email i received Undelivered Mail Returned to Sender😰

OO
Oluwatobi Owolabi #4

Make sure you have rDNS (PTR) DMARC, DKIM, SPF, MX properly configured

we
webby #7

Set PTR record for both IPv4 and IPv6. Also, make sure you are not using an IP as hostname.

we
webby #13

The quotes of the value should be removed. In most cases your domain key will return invalid.

SD
SaJeTek Developer #14

There are two things to fix here:

To remove “DST Root CA X3”

/root/.acme.sh/acme.sh --set-default-chain --preferred-chain “ISRG” --server letsencrypt

You then want to reissue the certificates for mail.seen-lami.com so the new certificate will exclude that store.

Secondly:
check /etc/postfix/main.cf

smtpd_tls_cert_file = some/path/to/cert.pem
smtpd_tls_key_file = some/path/to/key.pem

Mave sure both point directly or indirectly to /etc/letsencrypt/live/mail.seen-lami.com/fullchain.pem and /etc/letsencrypt/live/mail.seen-lami.com/privkey.pem respectively. You can use symlinks if required.

restart postfix

Rerun test and thank me later.

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