As-is: root@b:~# vim /etc/dovecot/conf.d/10-logging.conf root@b:~# sudo systemctl restart dovecot root@b:~# sudo mv /var/log/dovecot.log /var/log/dovecot.log.1 root@b:~# sudo doveadm log reopen root@b:~# ll /var/log/dovecot.log ls: cannot access '/var/log/dovecot.log': No such file or directory Upgrade: # apt install mail-stack-delivery Reading package lists... Done Building dependency tree Reading state information... Done The following package was automatically installed and is no longer required: libfreetype6 Use 'apt autoremove' to remove it. The following additional packages will be installed: dovecot-core dovecot-imapd dovecot-managesieved dovecot-pop3d dovecot-sieve Suggested packages: dovecot-gssapi dovecot-ldap dovecot-lmtpd dovecot-mysql dovecot-pgsql dovecot-solr dovecot-sqlite ntp The following packages will be upgraded: dovecot-core dovecot-imapd dovecot-managesieved dovecot-pop3d dovecot-sieve mail-stack-delivery 6 upgraded, 0 newly installed, 0 to remove and 14 not upgraded. Need to get 3289 kB of archives. After this operation, 1024 B disk space will be freed. Do you want to continue? [Y/n] Y Get:1 http://archive.ubuntu.com/ubuntu bionic-proposed/main amd64 dovecot-managesieved amd64 1:2.2.33.2-1ubuntu4.1 [41.6 kB] Get:2 http://archive.ubuntu.com/ubuntu bionic-proposed/main amd64 dovecot-sieve amd64 1:2.2.33.2-1ubuntu4.1 [311 kB] Get:3 http://archive.ubuntu.com/ubuntu bionic-proposed/main amd64 dovecot-pop3d amd64 1:2.2.33.2-1ubuntu4.1 [32.3 kB] Get:4 http://archive.ubuntu.com/ubuntu bionic-proposed/main amd64 dovecot-imapd amd64 1:2.2.33.2-1ubuntu4.1 [153 kB] Get:5 http://archive.ubuntu.com/ubuntu bionic-proposed/main amd64 dovecot-core amd64 1:2.2.33.2-1ubuntu4.1 [2740 kB] Get:6 http://archive.ubuntu.com/ubuntu bionic-proposed/main amd64 mail-stack-delivery all 1:2.2.33.2-1ubuntu4.1 [10.4 kB] Fetched 3289 kB in 1s (2986 kB/s) (Reading database ... 29440 files and directories currently installed.) Preparing to unpack .../dovecot-managesieved_1%3a2.2.33.2-1ubuntu4.1_amd64.deb ... Unpacking dovecot-managesieved (1:2.2.33.2-1ubuntu4.1) over (1:2.2.33.2-1ubuntu4) ... Preparing to unpack .../dovecot-sieve_1%3a2.2.33.2-1ubuntu4.1_amd64.deb ... Unpacking dovecot-sieve (1:2.2.33.2-1ubuntu4.1) over (1:2.2.33.2-1ubuntu4) ... Preparing to unpack .../dovecot-pop3d_1%3a2.2.33.2-1ubuntu4.1_amd64.deb ... Unpacking dovecot-pop3d (1:2.2.33.2-1ubuntu4.1) over (1:2.2.33.2-1ubuntu4) ... Preparing to unpack .../dovecot-imapd_1%3a2.2.33.2-1ubuntu4.1_amd64.deb ... Unpacking dovecot-imapd (1:2.2.33.2-1ubuntu4.1) over (1:2.2.33.2-1ubuntu4) ... Preparing to unpack .../dovecot-core_1%3a2.2.33.2-1ubuntu4.1_amd64.deb ... Unpacking dovecot-core (1:2.2.33.2-1ubuntu4.1) over (1:2.2.33.2-1ubuntu4) ... Setting up dovecot-core (1:2.2.33.2-1ubuntu4.1) ... (Reading database ... 29440 files and directories currently installed.) Preparing to unpack .../mail-stack-delivery_1%3a2.2.33.2-1ubuntu4.1_all.deb ... Unpacking mail-stack-delivery (1:2.2.33.2-1ubuntu4.1) over (1:2.2.33.2-1ubuntu4) ... Processing triggers for ufw (0.35-5) ... Processing triggers for ureadahead (0.100.0-20) ... Setting up dovecot-sieve (1:2.2.33.2-1ubuntu4.1) ... Setting up dovecot-pop3d (1:2.2.33.2-1ubuntu4.1) ... Processing triggers for systemd (237-3ubuntu10) ... Setting up dovecot-imapd (1:2.2.33.2-1ubuntu4.1) ... Processing triggers for man-db (2.8.3-2) ... Setting up dovecot-managesieved (1:2.2.33.2-1ubuntu4.1) ... Setting up mail-stack-delivery (1:2.2.33.2-1ubuntu4.1) ... Processing triggers for dovecot-core (1:2.2.33.2-1ubuntu4.1) .. # Issue resolved after restart and log reopen working: root@b:~# ll /var/log/dovecot.log -rw------- 1 root root 520 Jun 22 06:17 /var/log/dovecot.log root@b:~# sudo mv /var/log/dovecot.log /var/log/dovecot.log.2 root@b:~# sudo doveadm log reopen root@b:~# ll /var/log/dovecot.log -rw------- 1 root root 0 Jun 22 06:17 /var/log/dovecot.log