Common Email Errors and Configuration Solutions

Contents

SendAs Permissions

Steps to Apply Exchange 365:

Open > Admin Exchange 365 (https://admin.exchange.microsoft.com/)
Select on the left of the page, Recipients > Mailboxes
(1) Select Individual Mailbox and then (2) Manage mailbox delegation
Look for Send as and select Edit
Select Add permissions
Select the Service Account / System Email and then Save
Ensure, Mailbox permissions added
It’s important to note that these permissions can take 30 minutes to a half a day to apply, thanks Microsoft!

Steps to Apply Office 365:

Open > Admin Office 365 (https://admin.microsoft.com/)
Select Users > Active Users
Select the Individual Mailbox
On the right, select Mail > Mailbox permissions > Send as permissions
Select Add permissions
Select the Service Account / System Email
Select Add
Ensure Service Account / System Email saves and is present
It’s important to note that these permissions can take 30 minutes to a half a day to apply, thanks Microsoft!

Transport Rule / Bcc

BCC utilizing Regular Expression

Login to the Office 365 Admin Portal (https://portal.microsoftonline.com)
Select Admin then select Exchange
Under the Exchange Admin Center, select Mail Flow
Select the Rules tab
Select the + icon and select Create a new rule
1. Name: BCC w/ Regular Expression transport to Service Account
2. Apply this rule if: The subject or body matches:
  1. Paste each File ID Regex, eg… (PT\d\d\d\d\d\d\d)|(TEST-PT\d\d\d\d\d\d\d)
3. Do the following: Bcc the message to Service Account
Set the priority, audit, and mode criteria if needed.
Select Save
1. Note: Mail flow rules normally take at least 30-35 minutes to take hold in Office 365
Example: Bcc w/ (Microsoft) Regular Expression
1. https://docs.microsoft.com/en-us/previous-versions/office/exchange-server-2010/aa997187(v=exchg.141)?redirectedfrom=MSDN

BCC all to Service Account

Select Admin then select Exchange
Under the Exchange Admin Center, Then select Mail Flow
Select the Rules tab
Select the + icon and select Create a new rule
1. Name: BCC transport to Service Account
2. Apply this rule if: [Apply to all messages]
3. Do the following: Bcc the message to Service Account
Set the priority, audit, and mode criteria if needed.
Select Save
1. Note: Mail flow rules normally take 30-35 minutes to replicate in Office 365
Example: Bcc transport rule
1. https://manuals.gfi.com/en/mar12admin/content/administrator/topics/o365/o365configuringforwardingrule.htm

Common Resware SMTP issues

Error Message 5.7.3:

System.Net.Mail.SmtpException: Error in processing. The server response was: 5.7.3 STARTTLS is required to send mail [BYAPR21CA0015.namprd21.prod.outlook.com]

Steps to Fix:

Error Message 5.5.57:

at System.Net.Mail.MailCommand.CheckResponse(SmtpStatusCode statusCod

Steps to Fix:

Use SMTP checker online https://www.gmass.co/smtp-test
“Password Expired”
Needed to login to account for first time

Error Message 5.7.57 w/ 535 5.7.139:

System.Net.Mail.SmtpException: The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 Client not authenticated to send mail. Error: 535 5.7.139 Authentication unsuccessful, SmtpClientAuthentication is disabled for the Mailbox. Visit https://aka.ms/smtp_auth_disabled for more information.

Navigate to Microsoft 365 Admin Center > Users > Active Users > Select System Email
Select the Individual Mailbox
Select Mail
Select Manage email apps
Select Authenticated SMTP
Save