Not able to send emails to icloud

When trying to send emails to icloud, this is written on paniclog

2025-12-28 10:42:08 1vY7Kb-0323X5-1w SIGSEGV (fault address: 0x184)
2025-12-28 10:42:08 1vY7Kb-0323X5-1w SEGV_MAPERR
2025-12-28 10:42:08 1vY7Kb-0323X5-1w SIGSEGV (null pointer indirection)
2025-12-28 10:42:08 1vY7Kb-0323X5-1w SIGSEGV (489916 delivering 1vY7Kb-0323X5-1w to ``mx01.mail.icloud.com`` [17.42.251.62]/111.111.111.111 (``[email protected]``)
)
2025-12-28 10:42:08 1vY7Kb-0323X5-1w Delivery status for ``[email protected]``: got 0 of 7 bytes (pipeheader) from transport process 584946 for transport smtp

111.111.111.111 is a fake IP of the webserver and [email protected] is a fake email address

Any help is appreciated!

Only when sending to icloud or also to other domains?

Show the output of these commands:

exigrep '1vY7Kb-0323X5-1w' /var/log/exim4/mainlog*
grep -Ev '^(#|$)' /etc/exim4/update-exim4.conf.conf
ls -lart /etc/exim4
systemctl status exim4 --no-pager -l
dpkg -l | grep exim4
grep -E 'VER|ID' /etc/os-release

Is only happening to icloud.com and me.com which redirect to icloud.com

The server IP is listed at proofpoint for several weeks. I tried to delist it many times through https://www.proofpoint.com/us/ipcheck but they never answer my requests so I am not being able to remove it from proofpoint IP list. Any tips to delist it or at least receive an answer from them with a reason to being listed is much appreciated. I do not send SPAM at all!

After some check I determined that icloud uses proofpoint so it might be related.

+++ 1vY7Kb-0323X5-1w has not completed +++
2025-12-28 10:42:08 1vY7Kb-0323X5-1w Message is frozen

dc_eximconfig_configtype=‘local’
dc_other_hostnames=‘servername.domain.tld’
dc_local_interfaces=‘127.0.0.1 ; ::1’
dc_readhost=‘’
dc_relay_domains=‘’
dc_minimaldns=‘false’
dc_relay_nets=‘’
dc_smarthost=‘’
CFILEMODE=‘644’
dc_use_split_config=‘false’
dc_hide_mailname=‘’
dc_mailname_in_oh=‘true’
dc_localdelivery=‘mail_spool’

total 64
-rw-r----- 1 root Debian-exim 204 Mar 22 2025 passwd.client
drwxr-xr-x 9 root root 4096 May 13 2025 conf.d
-rw-r–r-- 1 root root 1040 May 13 2025 update-exim4.conf.conf
-rw-r–r-- 1 root root 0 May 13 2025 white-blocks.conf
-rw-r–r-- 1 root root 444 May 13 2025 system.filter
-rw-r–r-- 1 root root 0 May 13 2025 spam-blocks.conf
-rw-r–r-- 1 root root 4 May 13 2025 limit.conf
-rw-r----- 1 root Debian-exim 17 May 13 2025 srs.conf
-rw-r–r-- 1 root root 62 May 14 2025 dnsbl.conf
-rw-r----- 1 root Debian-exim 20682 May 14 2025 exim4.conf.template
drwxr-xr-x 2 root root 4096 Dec 29 12:09 domains
drwxr-xr-x 104 root root 4096 Dec 29 12:10 ..
drwxr-xr-x 4 root root 4096 Dec 29 12:23 .

exim4.service - LSB: exim Mail Transport Agent
Loaded: loaded (/etc/init.d/exim4; generated)
Active: active (running) since Mon 2025-12-28 10:42:08 WET; 2h 20min ago
Docs: man:systemd-sysv-generator(8)
Tasks: 1 (limit: 7064)
Memory: 19.3M
CPU: 1.340s
CGroup: /system.slice/exim4.service
└─584946 /usr/sbin/exim4 -bd -q30m

Dec 28 10:42:08 servername.domain.tld exim4[584946]: ALERT: exim paniclog /var/log/exim4/paniclog has non-zero size, mail system possibly broken
Dec 28 10:42:08 servername.domain.tld systemd[1]: exim4.service: Deactivated successfully.
Dec 28 10:42:08 servername.domain.tld systemd[1]: Stopped exim4.service - LSB: exim Mail Transport Agent.
Dec 28 10:42:08 servername.domain.tld systemd[1]: exim4.service: Consumed 1min 46.403s CPU time.
Dec 28 10:42:08 servername.domain.tld systemd[1]: Starting exim4.service - LSB: exim Mail Transport Agent…
Dec 28 10:42:08 servername.domain.tld exim4[584946]: Starting MTA: exim4.
Dec 28 10:42:08 servername.domain.tld exim4[584946]: ALERT: exim paniclog /var/log/exim4/paniclog has non-zero size, mail system possibly broken
Dec 28 10:42:08 servername.domain.tld systemd[1]: Started exim4.service - LSB: exim Mail Transport Agent.

ii exim4 4.96-15+deb12u7 all metapackage to ease Exim MTA (v4) installation
ii exim4-base 4.96-15+deb12u7 amd64 support files for all Exim MTA (v4) packages
ii exim4-config 4.96-15+deb12u7 all configuration for the Exim MTA (v4)
ii exim4-daemon-heavy 4.96-15+deb12u7 amd64 Exim MTA (v4) daemon with extended features, including exiscan-acl

VERSION_ID=“12”
VERSION=“12 (bookworm)”
VERSION_CODENAME=bookworm
ID=debian

That’s weird.

I didn’t even know about Proofpoint, so I have no idea.

I’m interested in the complete smtp conversation and that message is either in an older log or the log has been deleted. Could you please try sending a new email and capture the correct log?

The other outputs look fine.

I got this from an archived log

+++ 1vY7Kb-0323X5-1w has not completed +++
2025-12-28 10:42:08 1vY7Kb-0323X5-1w <= [email protected] H=servername.domain.tld [111.111.111.111] P=esmtpsa X=TLS1.2:ECDHE_SECP256R1__RSA_PSS_RSAE_SHA256__AES_128_GCM:128 CV=no SNI=servername.domain.tld A=dovecot_login:[email protected] S=687494 [email protected]
2025-12-28 10:42:10 1vY7Kb-0323X5-1w ``H=mx01.mail.icloud.com`` [111.111.111.111]: SMTP error from remote mail server after RCPT TO:<[email protected]>: 554 5.7.0 Blocked
2025-12-28 10:42:10 1vY7Kb-0323X5-1w SIGSEGV (fault address: 0x184)
2025-12-28 10:42:10 1vY7Kb-0323X5-1w SEGV_MAPERR
2025-12-28 10:42:10 1vY7Kb-0323X5-1w SIGSEGV (null pointer indirection)
2025-12-28 10:42:10 1vY7Kb-0323X5-1w SIGSEGV (584946 delivering 1vY7Kb-0323X5-1w to ``mx01.mail.icloud.com`` [111.111.111.111]/111.111.111.111 (``[email protected]``)
2025-12-28 10:42:10 1vY7Kb-0323X5-1w Delivery status for ``[email protected]``: got 0 of 7 bytes (pipeheader) from transport process 584946 for transport smtp
2025-12-28 10:42:10 1vY7Kb-0323X5-1w == ``[email protected]`` R=dnslookup T=remote_smtp defer (-1): smtp transport process returned non-zero status 0x000b: terminated by signal 11
2025-12-28 10:42:10 1vY7Kb-0323X5-1w Frozen
2025-12-28 10:45:00 1vY7Kb-0323X5-1w Message is frozen

As per this line

TO:<[email protected]>: 554 5.7.0 Blocked

I believe the reason is the proofpoint block

Yes, but Exim shouldn’t crash. It looks like a bug in Exim, but I’m using the same version and have never encountered that crash.

Once proofpoint is not delisting my IP and not answering my tickets I am considering to change de IP of the VPS. The VPS is in a proxmox server using a failover IP for this VPS.

I never changed an IP on a HestiaCP server, do you know what do I have to do to swap the Hestia server IP?

I guess I have to change all the DNS zones TTL to 5 minutes before making the change but don’t know what else do I have to do

I’m leaving now but I could answer in a couple of hours.

Meanwhile, if you don’t want to change the ip, you could use a smtp relay to send the mails from your domain, there are a few out there that are free for a limited amount of mails per day/month like brevo or smtp2go.

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Thank you very much for your help.

I am aware of SMTP Relay and I am using it on some domains but this VPS contains several domains and using SMTP Relay is not the best choice for me.

The command v-update-sys-ip is enough to swap the IP?

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Yes, it should be enough.

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