Office 365 mailboxes not autoreplying to external addresses

[Norphy]

Well, what the title says really.

 

My users are setting up OOF replies on their mailboxes. They work for internal mailboxes but not external ones.

 

I've checked our mail filter and they're not reaching it so I can only conclude that O365 is set to not allow them. The only setting that I can find is under Mail Flow/Remote Domains, the default rule (*) is there and there is a subsetting called "Out of Office replies configuration". It's set to External which suggests to me it's on. Using "Get-RemoteDomain -Identity default" in PowerShell returns the same.

 

Any suggestions?

 

Cheers,

 

Norphy

[Steve21]

Did they check the option for it to work on external ones too? There's 2 oof settings remember Unless the set to external one is checked too it only does internal

 

Steve

[Norphy]

A reasonable question and the first question I asked too. However, I've tried with one of my test accounts and yes, the option to reply to external addresses is checked. Using the "Get-MailboxAutoReplyConfiguration" cmdlet in PowerShell on the account in question returns "All" in the ExternalAudience" field.

[Steve21]

If you run

Get-mailbox -identity "email/user" | FL *forwarding*,*deliver* 

against one of the accounts, does it come back with anything?

 

Steve

[Norphy]

ForwardingAddress          : 
ForwardingSmtpAddress      : 
DeliverToMailboxAndForward : False

 

For my test and one of the affected users.

[Steve21]

That's fine, just forwarding rules auto disable OOF etc (same with transport rules)

 

and on the same user

Get-MailboxAutoReplyConfiguration -Identity "User/email"

 

Steve

[Norphy]

That's fine, just forwarding rules auto disable OOF etc (same with transport rules)

 

and on the same user

Get-MailboxAutoReplyConfiguration -Identity "User/email"

 

Steve

 

RunspaceId                       : 5285ce2c-9324-4039-81cd-4682ba4f7d91
AutoDeclineFutureRequestsWhenOOF : True
AutoReplyState                   : Scheduled
CreateOOFEvent                   : False
DeclineAllEventsForScheduledOOF  : False
DeclineEventsForScheduledOOF     : False
EventsToDeleteIDs                : 
EndTime                          : 20/12/2016 11:00:00
ExternalAudience                 : All
ExternalMessage                  : (snipped for brevity)
InternalMessage                  : (snipped for brevity)
DeclineMeetingMessage            : 
OOFEventSubject                  : 
StartTime                        : 19/12/2016 11:00:00
MailboxOwnerId                   : J.Kirk
Identity                         : J.Kirk
IsValid                          : True
ObjectState                      : Unchanged

 

It all looks OK to me.

[Steve21]

Aye that all looks fine. When you say your mail filter are you using a 3rd party piece for it?

 

Just wondering as OOF only replies once per user if it's something dumb hitting that with the same id etc. If you disable the OOF and instantly enable it and try again does it even reply once externally?

 

Steve

[Norphy]

We use Censornet. They act as a smart host for our outgoing email and they log everything that goes in and out. OOF emails aren't showing in the audit trail which makes me think that Office 365 isn't generating them. They're not showing in the message trace inside O365 either.

 

I enabled the OOF reply on my test user which worked perfectly when I emailed it internally but not from my external address. The test email got delivered but there was no automatic response.

 

/edit

 

Alright, scratch that, the message trace is showing the automatic reply. It's getting an "Unable to relay" error. It looks like it's my filter that's cocking things up after all.

 

The message trace shows it going to Microsoft's Exchange servers then it's saying

Reason: [{LED=550 Unable to relay };{MSG=};{FQDN=smtp2.scanscope.net};{IP=52.28.207.52};{LRT=12/19/2016 11:56:49 AM}]. OutboundProxyTargetIP: 52.28.207.52. OutboundProxyTargetHostName: smtp2.scanscope.net

 

when it tries to pass the message onto Censornet.

 

Gonna contact them now.

 

Thanks for your help

Edited December 19, 2016 by Norphy

[Steve21]

Is the spam filter in place as an outbound connector?

 

Get-SendConnector | FL Name,AddressSpaces,SourceTransportServers,SmartHosts

 

Steve

[Norphy]

I don't have a Get-SendConnector CmdLet but this is the result of the Get-OutboundConnector cmdlet:

 

RunspaceId                    : a9bd306e-b978-4fff-a7c1-64f103b2b14b
Enabled                       : True
UseMXRecord                   : False
Comment                       : 
ConnectorType                 : Partner
ConnectorSource               : AdminUI
RecipientDomains              : {*}
SmartHosts                    : {smtp1.scanscope.net, smtp2.scanscope.net}
TlsDomain                     : 
TlsSettings                   : 
IsTransportRuleScoped         : False
RouteAllMessagesViaOnPremises : False
CloudServicesMailEnabled      : False
AllAcceptedDomains            : False
TestMode                      : False
LinkForModifiedConnector      : 00000000-0000-0000-0000-000000000000
ValidationRecipients          : {snip}
IsValidated                   : False
LastValidationTimestamp       : 14/10/2016 16:24:48
AdminDisplayName              : 
ExchangeVersion               : 0.1 (8.0.535.0)
Name                          : Censornet Connector
DistinguishedName             : CN=Censornet Connector,CN=Transport Settings,CN=Configuration,CN=snip.onmicrosoft.com,CN=C
                               onfigurationUnits,DC=snip,DC=PROD,DC=OUTLOOK,DC=COM
Identity                      : Censornet Connector
Guid                          : d5c2c1e5-bf68-4227-a58e-a7f830303052
ObjectCategory                : snip.PROD.OUTLOOK.COM/Configuration/Schema/ms-Exch-SMTP-Outbound-Connector
ObjectClass                   : {top, msExchSMTPOutboundConnector}
WhenChanged                   : 14/10/2016 16:25:01
WhenCreated                   : 13/10/2016 13:44:41
WhenChangedUTC                : 14/10/2016 15:25:01
WhenCreatedUTC                : 13/10/2016 12:44:41
OrganizationId                : snip.PROD.OUTLOOK.COM/Microsoft Exchange Hosted Organizations/snip.onmicrosoft.com 
                               - snip.PROD.OUTLOOK.COM/ConfigurationUnits/snip.onmicrosoft.com/Configuration
Id                            : Censornet Connector
OriginatingServer             : snip.PROD.OUTLOOK.COM
IsValid                       : True
ObjectState                   : Unchanged