IBM cloud port 25 Sendgrid email services

IBM cloud offers sendgrid email delivery services for your SMTP TCP port 25 applications hosted on IBM cloud. This is because the most common port for SMTP, the port 25 for outbound connections for sending email is not allowed on IBM cloud and several other cloud providers, this is due to too many abuse cases in the past – IBM Cloud says – As of 28 October 2015, IBM Cloud no longer allows outbound connections through TCP port 25 (SMTP) on new accounts:- https://cloud.ibm.com/docs/email-delivery?topic=email-delivery-email-delivery-faw#can-i-use-outbound-email-on-port-25-

On IBM Cloud I am running an exchange 2016 test environment and to be able to perform outbound SMTP connections, I need to have port 25 open, as well as other SMTP ports. We now know IBM cloud blocks outbound port 25, and offers sendgrid email service as an alternative.

I will show you how to setup sendgrid email services, and configure your send connector on Exchange to use sendgrid as a smarthost, to allow you to relay email to sendgrid and from sendgrid it will send your email externally using port 25. You can have a free sendgrid account from IBM Cloud if you plan to send less than 25,000 emails per month. If you need to send more, here are the pricing options:-

  1. To begin, go over to your IBM cloud dashboard, expand the navigation menu on the top left

expand the pin, classic infrastructure and scroll down to services – click open Email delivery

you will see the button to order email delivery

2. Choose the option for free package if you plan to send less than 25,000 a month or any of the pricing options depending on your need as i previously showed in above screenshot. Once done and your service is online, it will appear under Email delivery service with options to view your account details and settings.

3.

Click the check mark button to Enable SMTP, and then expand the Actions arrow to show more options:-

4. We can go directly to sendgrid access portal, by clicking on it:-

Configure Exchange 2016 to use sendgrid

5. To configure your email application on IBM Cloud to use sendgrid as smarthost for SMTP relay, from the sendgrid dashboard, on the left side, click on Email API and then >> Integration guide >> SMTP Relay

6. Follow the steps to name and create and API key, take note of your API key string which will also be your password, so, username and password, server name. As for ports, since we cannot use port 25 on IBM cloud, we can use port 465 or 587 to relay messages to sendgrid. leave this dashboard open we will come back later once exchange side is done.

7. Login to your exchange admin center EAC, go to mail flow >> send connectors, create a new send connector for sendgrid, click + to add new send connector :-

name your send connector, type – custom,

Under network settings, select route mail through smart hosts, click on the + to add the sendgrid server name:-


Add smtp.sendgrid.net , the servername that we copied from the sendgrid dashboard, click on next

Next, select Basic authentication, choose offer basic authentication only after starting TLS for security, enter your username and password you copied from the sendgrid dashboard earlier

Click the + to add your source server – your exchange server that will be responsible for sending mail to sendgrid and once done, click finish to create your new send connector, which will be visible in your EAC send connectors. Make sure it is enabled.

8. By default your new exchange send connector will use port 25, so we have to change this to port 587, to do this, we need to run below command from exchange management shell

Set-sendconnector -identity “name of your newly created send connector” -Port 587

Once done, you can do Restart-service MSExchangetransport to make sure your changes take effect immediately.

You are done. Go over to your sendgrid dashboard that we left open and do the final steps, tick i’ve updated my settings and verify.

Test sending email from Exchange.

Now all your outbound emails from Exchange will use your new send connector to relay messages to sendgrid and from sendgrid it will be sent to your recipients. From your sendgrid dashboard you can view all the statistics for your messages. Also you can study the message header of your email to see how the message was routed to external recipient.

For all other SMTP applications other than Exchange, you can refer to sendgrid documentation on how to configure this for your application – https://sendgrid.com/docs/for-developers/sending-email/getting-started-smtp/

Thanks, I hope you found this useful, feel free to comment and add suggestions.

Winmail.dat attachment

Content-Type: application/ms-tnef; name="winmail.dat"

Winmail.dat attachment – One of my user sending emails from Outlook application and Exchange online office365 complains the recipient is receiving a winmail.dat attachment in every email she sends to one specific recipient domain, however, the same email is received by yahoo and other email domain without any winmail.dat attachment. Sender has tried setting her outlook to ensure ‘only plain text’ is used when composing email but still recipient is getting winmail.dat. So why is this one specific recipient domain getting winmail.dat attachments even when outlook has been set to use only plain text?

Solution:

1. Make sure to get more details if you can about the recipient domain mail system, for me I found out from their website that they recommend ‘plain text’ emails over html or rich text, as their mail system can have problems decoding other mail formats.

2. Check the message email headers of your sender, you can see the content-type showing “winmail.dat” instead of content-type “plain text” :-

Content-type in Message header of email sent that contains winmail.dat:-

Content-Type: application/ms-tnef; name="winmail.dat"

Content-type in Message header of email sent that uses plain text and does not contain winmail.dat:-

Content-Type: text/plain; charset="us-ascii"

3. What is winmail.dat?

Outlook and Exchange uses the Transport Neutral Encapsulation Format (TNEF) format for your emails that contains rich text format (RTF), RTF files offer some formatting features like bold, italic, underline, bullets, different fonts, and text justification. Messaging systems that aren’t based on Microsoft Exchange may be unable to interpret messages that use this rich text format. If the recipient’s messaging system can’t process this format, a file attachment that’s called Winmail.dat is added to the message.

Note: By default, email messages that are sent from Exchange Online in Office 365 use the Transport Neutral Encapsulation Format (TNEF) format

4. If your recipient domain email system cannot decipher TNEF and a winmail.dat is received, then Office 365 admins can use Exchange online PowerShell to change the message format to prevent the Winmail.dat attachment from being sent to those external recipients. To do this:-

Connect to Office365 Exchange Online using Remote PowerShell

  1. Run the following Windows PowerShell commands to configure the message format as plain Text Only for a specific external recipient:
Set-MailContact <ExternalEmailAddress or GUID> -UseMapiRichTextFormat Never
Set-MailContact -Identity <ExternalEmailAddress or GUID> -UsePreferMessageFormat $True 

Run the following Windows PowerShell command to confirm that the message format was applied:-

Get-MailContact | Select <ExternalEmailAddress or GUID> | Select UseMapiRichTextFormat

2. To Change the message format for all messages that are sent to a specific domain
This method requires you to create a remote domain object in Exchange Online to control how messages are sent to external domains. You can also use this method to change the message format for messages that are sent to coexistence domains.

Connect to Office365 Exchange Online using Remote PowerShell

Run the following Windows PowerShell command to create a remote domain for an external domain:

New-RemoteDomain -Name <Name of External Domain> -DomainName 

Run the following Windows PowerShell command to prevent messages from being sent in rich text format:

Set-RemoteDomain -Identity <Name of Domain> -TNEFEnabled $false 

Run the following WindowsPowerShell command to check that the setting was applied:

Get-RemoteDomain -Identity <Name of Domain>| Select TNEFEnabled 

More info on Microsoft docs – https://docs.microsoft.com/en-us/exchange/mail-flow/content-conversion/tnef-conversion?view=exchserver-2019

MailNonUniversalGroup – Distribution List

Happy New year 2020. I wish you more progress this year from where you left off last year. Now let’s dive right to our topic on MailNonUniversalGroup distribution list. So i had a case where users where complaining of not receiving emails sent to a distribution list. After several minutes tracing the messages, it came to a halt with the following interesting details from the trace log:-

——–

Source : ROUTING
EventId : DROP

RecipientStatus : {[{LED=250 2.1.5 RESOLVER.GRP.Expanded; distribution list expanded};{MSG=};{FQDN=};{IP=};{LRT=}]}

——–

Some further digging and here is what i found for the distribution group that was not receiving emails:-

Get-DistributionGroup "nameofmydistributionlist" | fl recipienttypedetails

RecipientTypeDetails : MailNonUniversalGroup

Result shows my distribution group was of type: MailNonUniversalGroup

Further checking on when this group was first created in AD, shows far back as of 2012, and this must have been when it was migrated from previous legacy exchange 2003 to exchange 2010 but was not upgraded to a universal group at that time.

Microsoft recommends to convert all legacy exchange distribution groups to “universal” groups for use on Exchange 2010/2013/2016/2019 especially if you want to have all the features of distribution groups included.

In my case the distribution group members where on office365 and they needed to receive external email sent to the email address of the distribution list.

To solve, change the distribution group from MailNonUniversalGroup to Universal, I did this via exchange powershell:-

Get-DistributionGroup "nameofmydistributionlist" | Set-Group -Universal

wait a few minutes for replication and check again using:-

Get-DistributionGroup "nameofmydistributionlist" | fl recipienttypedetails

RecipientTypeDetails : MailUniversalDistributionGroup

It has now been converted to MailUniversalDistributionGroup

Now we can receive emails sent to the distribution list without any issues.

Tip: To do this in bulk for all your distribution groups that was just migrated over from legacy exchange versions 2003/2007, you can use the following command which will change all mailnonuniversalgroups to universal:-

Get-DistributionGroup -ResultSize unlimited -RecipientTypeDetails mailnonuniversalgroup | Set-Group universal

and then to apply the upgrade :

Get-DistributionGroup -ResultSize unlimited | Set-DistributionGroup -ForceUpgrade

Mail.Que database too large

In this troubleshooting you will learn how to safely delete and recreate the Exchange server transport queue database file “mail.que” and get tips to determine the root cause of your growing mail.que. On deletion of the mail.que file, Exchange will auto create a new mail.que file once you restart the Microsoft Exchange transport service. This applies to Exchange 2010,2013,2016,2019

Below solution will help you avoid messaging downtime, if your mail.que file is getting too large or consuming a lot of space on your disk drive at a critical stage which can cause major impact to mail flow or even Exchange auto shutting down its services, however, be sure to later properly investigate the root cause of the mail.que file growth as it can reoccur. Some known causes of mail.que file growth can be due to organization wide Exchange transport configurations such as the maxdumpstertime(exchange 2010), safetynetholdtime, pipeline tracing value, etc – For me, the safetynetholdtime value on Exchange 2016 was set to 7 days, which resulted in the growth of mail.que as it holds copies of successfully submitted messages for 7 days, another thing was that my day to day mail flow to my Exchange infra had increase from what it used to be several months ago , so i decided to schedule maintenance and expand the disk space where my mail.que resides from 250GB to 500GB , and ever since i no longer have mail.queue space issues. It might also be good to go back to your Exchange Server Role Requirements Calculator to help you determine where you are lacking in terms of disk space requirements, number of inbound messages to your infra etc. and from there you can make adjustments.

By default  your mail.que file location should be at :-  %ExchangeInstallPath%TransportRoles\data\Queue

screenshot-20190116165503-667x215

First, using Exchange powershell we can check the existing size in GB of mail.que, so open up your EMS on the affected Exchange server and run the following:-

Get-ChildItem "D:\Exchange Server\TransportRoles\data\Queue\mail.que" |select name,@{Label="size";Expression={"{0:N0}" -F ($_.Length/1GB)}}

screenshot-20190116161259-906x110

To Solve:-

  1. Put your Exchange server in maintenance mode, if you have SCOM etc, or schedule out-of- office hour maintenance before you proceed to perform these actions.
  2. Suspend Microsoft Exchange Transport service, (NOT STOP). This will drain and allow the current messages in the queue to be processed before it stops accepting new messages to the queue. To do this, on EMS run:- Suspend-service -name "Microsoft Exchange Transport"
  3. Run :- Get-queue  – to check and ensure messages in queues are empty (0).
  4.  Do not worry about shadow redundancy queues, these are fine if it has queues.
  5. Next, stop the MS Exchange transport service, :- Stop-service -name "Microsoft Exchange Transport". Once it has stopped give an extra 5 minutes for everything to settle in.
  6. Open the mail.que location ( %ExchangeInstallPath%TransportRoles\data\Queue) , select all files inside the folder and delete it, optionally you can move it to an external drive with enough space, you can rename it to something like mail.que.old as a backup.
  7. Now, After you have completed above steps. on Exchange management shell enter:- Start-service -name "Microsoft Exchange Transport"
  8. You will see a new mail.que file is auto created by Exchange, and your drive space released and back to normal.
  9. Run on EMS, Get-queue  – to check and monitor and ensure mail flow is back to normal. Above actions will save you from exchange running out of space and shutting down services automatically, and also gives you more time to investigate further on the root-cause of the growth, check event logs, google, technet articles, for more troubleshooting. Good luck.

Tip: use a tool such as Treesize free to get a detailed view of files and the size in your drive. It can come in handy when you want to check the size of files in your exchange server data path.

P.S: Watch out for my next article where I will show you how to change the default directory for your mail.que database, for me I prefer to put it on D:\ or another drive, which is separate from Exchange installation path on C:\ and OS. This is a very good recommendation because you can focus on troubleshooting and increasing the disk space for the mail.que on D:\ without touching your System/Exchange on C:\ drive, also allowing it to be stored on a separate drive from C:\ allows it to make use of the resources on that drive alone.

Cannot set the security descriptor of mailbox

You may come across this error in powershell – Cannot set the security descriptor of mailbox…. For me it was occurring in the beginning when we were doing a small number of mailbox migrations from Exchange 2010 to Exchange 2016 and assigning mailbox permissions.

Screenshot_1

“Cannot set the security descriptor of mailbox…….. in exchange mailbox database ……..”

Error appeared when I used below exchange powershell command to grant full access permission to userB on userA mailbox:-

Add-MailboxPermission -Identity "userA" -User "userB" -AccessRights FullAccess -InheritanceType All

Cause:-

Changes in user attributes in AD after migrating user from Exchange 2010 to Exchange 2016.

Powershell is throwing this error because the mailbox that you are trying to add the full access permission is now hosted in a higher version of exchange than the server you are running the powershell command from.

In my case, it means i should be running the Add-MailboxPermission command above in Exchange 2016 exchange management shell where the mailbox of userA is now hosted after it was migrated from Exchange 2010.

Solution:-

  1. Check which database the mailbox is currently on, and which version of Exchange server.

Get-Mailbox -Identity UserA | fl database,exchangeversion

2. Use Exchange powershell on a higher version of  exchange where the mailbox now resides after migration. If mailbox was migrated from Exchange 2010 to Exchange 2016, so you will have to run the command from Exchange 2016 management shell to add the permissions successfully.

Add-MailboxPermission -Identity "userA" -User "userB" -AccessRights FullAccess -InheritanceType All

You can always refer to this Microsoft technet link to know your versions of Exchange from the exchangeversion result you get 🙂 

https://technet.microsoft.com/en-us/library/hh135098(v=exchg.150).aspx

Leave a comment and let me know if it worked for you.