I've recently migrated services to a new mailserver, which has of course 
promptly started kicking out dire errors that didn't show during testing.

Here's an example transcript, postconf -n is below

Out: 220 gilded-bat.laughingboot.net ESMTP Postfix
In:  EHLO [10.2.45.174]
Out: 250-gilded-bat.laughingboot.net
Out: 250-PIPELINING
Out: 250-SIZE 6291456
Out: 250-ETRN
Out: 250-STARTTLS
Out: 250-ENHANCEDSTATUSCODES
Out: 250-8BITMIME
Out: 250 DSN
In:  STARTTLS
Out: 454 4.7.0 TLS not available due to local problem
In:  ???
Out: 502 5.5.2 Error: command not recognized
In:  ??????????????????????????????
Out: 502 5.5.2 Error: command not recognized
In:
Out: 500 5.5.2 Error: bad syntax

If there's more information in the logs, I'm not finding it, but I'm relatively 
inexperienced with postfix and so may well be missing something.

I'd be happy to disable SSL/TLS for now, just to get things running clean.

Thanks for any help you can provide.  I'm not sure how to proceed.

-Bryan


address_verify_map = hash:$data_directory/verify_cache
address_verify_sender = postmas...@laughingboot.net
biff = no
command_directory = /usr/sbin
config_directory = /etc/postfix
content_filter = smtp-amavis:[127.0.0.1]:10024
daemon_directory = /usr/libexec/postfix
debug_peer_level = 2
disable_vrfy_command = yes
enable_server_options = yes
header_checks = pcre:/etc/postfix/custom_header_checks
html_directory = /usr/share/doc/postfix/html
inet_interfaces = all
mail_owner = _postfix
mailbox_size_limit = 0
mailbox_transport = dovecot
mailq_path = /usr/bin/mailq
manpage_directory = /usr/share/man
message_size_limit = 6291456
mydestination = $myhostname     localhost.$mydomain     localhost
mydomain = laughingboot.net
mydomain_fallback = localhost
myhostname = gilded-bat.laughingboot.net
mynetworks = 127.0.0.0/8        65.101.147.66   75.146.60.115   75.146.60.123   
75.146.60.124   75.146.60.125
newaliases_path = /usr/bin/newaliases
owner_request_special = no
permit_mx_backup_networks = $mynetworks
queue_directory = /private/var/spool/postfix
readme_directory = /usr/share/doc/postfix
recipient_delimiter = +
relay_domains = hash:/etc/postfix/relay_domains
relay_recipient_maps = 
relayhost = 
sample_directory = /usr/share/doc/postfix/examples
sendmail_path = /usr/sbin/sendmail
setgid_group = _postdrop
smtpd_client_restrictions = permit_sasl_authenticated permit_mynetworks 
reject_rbl_client zen.spamhaus.org permit
smtpd_data_restrictions = permit_mynetworks     reject_unauth_pipelining        
reject_multi_recipient_bounce   permit
smtpd_enforce_tls = no
smtpd_helo_required = yes
smtpd_helo_restrictions = permit_sasl_authenticated     permit_mynetworks       
check_helo_access hash:/etc/postfix/helo_access reject_non_fqdn_helo_hostname   
reject_invalid_helo_hostname    permit
smtpd_pw_server_security_options = cram-md5,login,plain,gssapi
smtpd_recipient_restrictions = reject_non_fqdn_recipient        
reject_unknown_recipient_domain permit_mynetworks       
permit_sasl_authenticated       permit_mx_backup        
reject_unauth_destinationcheck_policy_service unix:private/policy       
reject_non_fqdn_hostname        reject_invalid_hostname 
reject_unlisted_recipient       reject_rhsbl_recipient zen.spamhaus.org 
warn_if_reject reject_unknown_recipient_domain  warn_if_reject 
reject_unverified_recipient      permit
smtpd_sasl_auth_enable = yes
smtpd_sender_restrictions = permit_sasl_authenticated   permit_mynetworks       
reject_non_fqdn_sender  reject_rhsbl_sender zen.spamhaus.org    
reject_unknown_sender_domain    reject_unverified_sender        permit
smtpd_tls_exclude_ciphers = SSLv2       aNULL   ADH     eNULL
smtpd_tls_loglevel = 0
smtpd_use_pw_server = yes
smtpd_use_tls = no
soft_bounce = no
tls_random_source = dev:/dev/urandom
unknown_local_recipient_reject_code = 550
virtual_alias_domains = $virtual_alias_maps     
hash:/etc/postfix/virtual_domains
virtual_alias_maps = hash:/etc/postfix/virtual_users

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