Out of office reply not sending reply - outlook-2010

I have one user out of several who sets his out of office reply in Outlook/Outlook Web Access and when he receives an email the sender does not receive a reply. Send to External senders is checked. Is there a good way to correct this? This is on SBS 2008 and Exchange 2010.

I ran outlook.exe /cleanrules CAUTION: It wipes all of the rules.

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Exchange server mail interceptor (connector/delivery agents/mailflow)

My basic requirement is that I need to create "something" that is capable of intercepting emails incoming/outgoing from our mail server. It cannot be an extension to mail clients. Currently we consider only exchange server. In my research I found below resources that seems to be helpful.
Mail flow and the transport
Delivery agents and Delivery Agent connectors
Transport agents
From these transport agents seems to be quite old. Now I can't figure out what's the best from the remaining options(Mail flow and the transport or Delivery agents and Delivery Agent connectors).
Whatever I develop should be able to read email get some statistics (using mail header(s), amount of attachments etc...) and store it into a custom database. Additionally add some custom headers to incoming/outgoing mails.
Can anyone point me to right direction? Should it be some kind of a service that I can install in Exchange server? (admin center->mail flow-> connectors). For example, can I write it in c# and host it like an assembly? or may be a web hook to a hosted service where Exchange will forward emails in real time etc...
I couldn't find any examples/tutorials except this
If its OnPrem Exchange and you don't have or are considering Office365 then Transport Agents would be the right thing to use. They haven't change since 2013 but are still what is used for this type of thing the last SDK was 2010 but its still valid given the lack of change on the backend https://learn.microsoft.com/en-us/previous-versions/office/developer/exchange-server-2010/dd877026(v=exchg.140)
Delivery Agents are more for when you have an external gateway that you want to send and receive messages from.

Exchange ActiveSync - get unseen emails count

I am writing Exchange ActiveSync client in C++. I use FolderSync command for synchronize list of folders and Sync command for synchronize emails from server.
In IMAP protocol I use command STATUS INBOX (UNSEEN) for getting unseen emails in inbox folder.
Is in Exchange ActiveSync some equivalent command ?
According to the Microsoft documentation only the following is part from ActiveSync:
Support for HTML messages
Support for follow-up flags
Conversation grouping of email messages
Ability to synchronize or not synchronize an entire conversation
Synchronization of Short Message Service (SMS) messages with a user's Exchange mailbox
Support for viewing message reply status
Support for fast message retrieval
Meeting attendee information
Enhanced Exchange Search
PIN reset
Enhanced device security through password policies
Autodiscover for over-the-air provisioning
Support for setting automatic replies when users are away, on vacation, or out of the office
Support for task synchronization
Direct Push
Support for availability information for contacts
But you might wish to implement something via EWS (see here some example).

Exchange 2010 is sending emails from accounts that do not exist?

All of a sudden, our exchange server has started sending out emails to .com.br addresses from accounts that do not exist in our organization. For example:
sadfjkh32#myorganization.com
sasdfsdkh4352#myorganization.com
sadhdf#myorganization.com
Please help.
You should review your recieve connector configuration to make sure you are not allowing someone to relay mail over your server.
Aditionally use the message tracking in esm and look for those emails.
Try to find the source IP address of those emails, meaning where they are generated.
Are they generating from an application server on your network. Maybe a scanner device, a pc...
As soon as you find the ip address you will have a better idea what is going on
Liran Zamir

hMailServer only replies on first time

I've just installed hmail on Windows 2012 to self host a mail server. Opened the ports (25, 143 - SMTP, IMAP). Setup auto reply on some test accounts on domain.
I have a strange experience: The first emails I send to the new inboxes from my gmail account get auto-replied. Thereafter any more emails sent are largely not replied (i.e. mostly not replied but occassionaly very late). The hMailServer logs show it found the emails and sending the replies. I tried with my work email account to the new hMailServer inboxes and its the same situation.
I've checked the spam and they only occasionally go in there depending on the auto reply message body. Reverse DNS has been setup by my cloud instance provider.
Not sure whats going on but the hMailServer diagnosis does show red lights against MX records not being found local and internet domains (although internet MX route checking sites give it a green light when checking).
Why is it only sending out first time and then less likely other times.
Ok its because the autoreply function only sends auto replies once per email address. I ended up applying a 'rule' instead to reply and delete the incoming the message to reach the desired behaviour.
The autoreply feature only ONCE per email address PER SESSION. That is to say, when hmailserver (service) is stopped and restarted the cache is cleared and so the first occurrence of the autoreply already sent is forgotten. (Note: it also doesnt autoreply to 'auto-reply' emails as this could cause looping)

How can I send mail with SMTP and see the mail in the Outlook outbox?

We have a new Exchange server and use SMTP to send mails over it. This works so far, but we have no idea how the SMTP mail can be configured so that the outbox in Outlook 2003 of the sender account shows this mail. Is this only possible using MAPI or other mail client protocols?
Yes, email sent via SMTP will not be stored in the Exchange database. The simple way to work around it would be to automatically BCC the sender on any email sent via SMTP. It wouldn't be perfect as it would look like an incoming email, but at least the information would be there.
There might be addon products that you could buy that would listen in on any SMTP traffic and automatically create "sent items".
But the best solution would be something like Exchange Web Services, CDO or MAPI (depending on what your needs are and what software versions you're using).
If the accounts are IMAP accounts, you can use that to put the mail into the Sent folder. Otherwise, you'll have to use the Microsoft protocols like MAPI.

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