How to set up an Auto Responder or Automatic Replies for an Alias in O365 Exchange

When you manage a large amount of Exchange mailboxes, inevitably someone will leave the organization, and you have to setup autoreplies with a message stating the user is no longer available by email. Common sense dictates we will setup a [email protected] mailbox and add the terminated users as alias’ to that mailbox, but not so fast. After a few days of testing and working with support, we’ve found that setting up a shared mailbox with autoreplies enabled with the terminated user’s unique email address/alias, provides the most consistent results.

We’re not going to go through the myriad of possible scenarios about what your org does with a mailbox after a user leaves. Instead, we’ll assume the mailbox is now deleted, and forwarding of mail bound for that mailbox is no longer necessary. To be on the safe side, ensure you back up the mailbox in some way before deleting the mail.

When testing auto replies, you may want to use the Exchange Message Tracker to see the messages come in and go out. To get there, go to O365 Admin > Exchange > Mail Flow > Message Trace.

A good thing to note here is that while performing a message trace, when sending test messages to the newly created shared mailbox with Automatic Replies enabled from within the same tenant or domain, auto reply messages may Drop with the following error:

Date/Time DropReason: [{LED=250 2.1.5 RESOLVER.OOF.ExtToInt; handled external OOF addressed to internal recipient};{MSG=};{FQDN=};{IP=};{LRT=}]

This Drop message is actually an intended action, and is not an error, as it is probably used to prevent a loop of autoreplies within the same tenant.

Getting back to our original issue, to generate autoreplies, we first tried to setup a “[email protected]” shared mailbox and add terminated user’s email addresses as aliases to the noreply box, but we got inconsistent results. Instead, we did the following.

How to Setup Automatic Replies for a Terminated User Mailbox

  • Create a shared mailbox with the terminated user’s email address. To do this go to 365 Admin Center > Groups > Shared mailboxes > Add a shared mailbox > Give the shared mailbox a name like “JDoe Term AutoReply” > Give the shared mailbox the (previously/actually used) email address of the terminated user. This does not use a mailbox license thereby freeing up a license. Alternatively, you can try simply converting the terminated user’s mailbox to a shared mailbox, but we had an inconsistent result doing this.
  • Next, simply click on the details of the shared mailbox, and under Automatic replies, click the Edit link:

Next place Checkmarks in both “Send automatic replies to senders inside this organization” and “Send automatic replies to senders outside this organization”

Add a reply blurb which can be something similar to the following:

The Representative you are trying to contact is no longer affiliated with this Corporation. You will be receiving communication with more information pertaining to the transition of the Representative on your account. If you have an urgent matter and would like to speak with someone, please call our Service Center at 800-555-5555 between the hours of 6am-5pm (PST).

Click “Save” at the bottom and you should be all set.

If you want to test, you can try sending an email from an account outside your organization. *Note – when we sent a test message from gmail, the autoreply ended up going into the gmail account’s spam folder.

If further errors are encountered, you may need to look at your spam/external forwarding policies in your mail filtering site at https://protection.office.com/antispam or reach out to MS Support.

Hacked Office 365 Outlook Account cannot send or receive email

Recently a client complained that an Office 365 account had sent out spam messages to a number of clients. Later, the suspect account which had been sending spam could no longer send or receive email. However upon first glance at the mailbox, sent messages were sitting in the sent items folder, and messages sent to the account in question were not receiving bounce-back failures, but the messages sent to the affected account were not in the inbox. After we changed the password to the account, and enabled 2FA on the account we could still not send and receive mail. Below are the steps used to resolve this particular issue. In short, a malicious inbox rule had been created and outbound messages had been blocked by Microsoft.

  1. Log into the tenant’s Admin console with an Administrative account, and change the password of the affected account.
  2. Log into the affected account as the user using the new password.
  3. Click on the Gear icon and then under Your app settings, click Mail.

4. One in the Mail app Settings, go to Mail > Automatic Processing > Inbox and Sweep rules.

Here we can see a malicious rule had been created to mark all inbound mail as Read and move the message to the “RSS Subscriptions” folder:

5. Uncheck and turn off any malicious or invalid rules.

Also check for any new forwarding rules in Mail > Accounts > Forwarding:

6. When we look in our “RSS Subscriptions” folder we find some messages from Microsoft indicating the account has been blocked from sending mail because the account was flagged as sending spam:

Your message couldn't be delivered because you weren't recognized as a valid sender. The most common reason for this is that your email address is suspected of sending spam and it's no longer allowed to send messages outside of your organization. Contact your email admin for assistance.

Remote Server returned '550 5.1.8 Access denied, bad outbound sender. For more information please go to http://go.microsoft.com/fwlink/?LinkId=875724. S(9333) [DM5PR10MB1914.namprd10.prod.outlook.com]'

7. To resolve this issue, we’ll need to go into the Action Center. Log into the Admin console > Admin Centers > Exchange > Protection > Action Center

8. In the Action center, we’ll find an issue flagged regarding our hacked user account. Take action on the issue and after a while due to permission propagation, it may take up to 2 hours for the account to be re-enabled for sending mail again.

9. It might be a good idea to contact Microsoft Support if you continue to experience problems with a user account sending spam. Changing the password should prevent malicious access. Most like the account had been phished or the computer the user has was compromised by a virus/malware or spyware. It’s recommended that the account have two-factor authentication or multi-factor authentication enabled to prevent the account from being hacked again.

tag: outlook cannot send or receive email but sent mail is in sent items folder

Spammy phone calls from 281-806-5695, 725-696-3397, 650-722-1909

Apparently I am approved for a large loan for my business, although I don’t even own a business… block these numbers too: 281-806-5695 , 725-696-3397 from yesterday, and from the day before,  650-722-1909 . I wonder why I seem to be getting so many of these spam phone calls when there are heavy penalties for violating the “Do not call” list? Time to check the National Do Not Call registry again and re-register.

If you’re also getting annoying spam calls from these numbers please go to https://complaints.donotcall.gov/complaint/complaintcheck.aspx and file a complaint.