iPhone/iPad - Cannot send mail. A copy has been placed in your Outbox. The recipient was rejected by the server

Occasionally I've seen users experience an issue where they can no longer send emails to anyone from their iPad or iPhone, they get the below error message;

"Cannot send mail. A copy has been placed in your Outbox. The recipient %name% was rejected by the server"

The issue is usually caused by the authentication (ie. username and password) failing for the email account, because it is either missing or incorrect.

I've often seen this happen after iOS updates, as passwords for email accounts aren't always preserved during the update process. As a result, the password appears to be present (when you check the settings), but actually isn't, and therefore emails won't send any longer.

To fix the issue, do the following on the problematic device(s);

• Go to Settings
• Go to Mail
  
  
• Select Accounts
  
  
• Select the account that you are having problems sending from
  
  
• Select the account again (first option at top of screen)
  
  
• Update the Domain, Username and Password fields. Even if the password appears to be in there (represented by black circles), delete whatever is in there and re-type the password
  
  
• Click Done from the top right corner. Settings should now be checked and you should get a list of ticks down the ride side of the page

If the settings saved successfully you can try sending emails again, it should now work correctly.

Check which Exchange Mailboxes a User has Full Access or Send As Permissions On using Powershell

As an exchange administrator, you may occassionally need to know which mailboxes a particular user has Full Mailbox Access or Send As permissions to. This may be required as part of an audit, or to simply copy an existing users permissions for a new user you are setting up/creating.

The script below helps to accomplish this, as there is no in-built/easy way to view which mailboxes a particular user has access to - ie. Full Mailbox Access, or Send As permissions

First you need to specify the user whose existing access we are checking, using the $user variable. We use the wildcard "*" to essentially match any name that contains what is between the *'s - the users first name, last name or alias should work.

$user = "*peter*"

Next we run the get-mailbox cmdlet against all mailboxes in exchange, to query the permissions on each mailbox to see if this user exists in the respective permissions list.

There are two separate commands to do this - one to check for Full Access permissions, and the other to check for Send As permissions

get-mailbox -resultsize unlimited | get-mailboxpermission | where {$_.user -like $user} | select Identity, AccessRights

get-mailbox -resultsize unlimited | get-adpermission | where {($_.user -like $user) -and ($_.ExtendedRights -like "*Send-As*")} | select Identity, ExtendedRights

If any matches are found, the results will be displayed showing their Identity (ie. name) and the Access Rights level they have

Sending Email Messages with Powershell

A lot of the scripts I use generate reports or .csv files that I need to reference or send to other users who have requested them. One of the easiest ways to accomplish this is to configure your script to automatically email yourself (or anyone else) with the results and/or any files that were created in your script. This saves you time by not having to manually copy the files to another location or attach them to a new email message. You can simply receive the email message and forward it on, or include all recipients in the original email sent by the script.

The following lines of code can be used to create and send an email message with Windows Powershell:


$SmtpClient = new-object system.net.mail.smtpClient 
$MailMessage = New-Object system.net.mail.mailmessage 
$SmtpClient.Host = "your.smtp.server" 
$mailmessage.from = ("fromaddress@yourdomain.com") 

$mailmessage.Subject = “Subject”
$mailmessage.Body = "body text"
$mailmessage.IsBodyHtml = $true
$mailmessage.ReplyTo = "replytoaddress@yourdomain.com"
$mailmessage.Attachments.Add("C:\Path\yourfile.txt")
$smtpclient.Send($mailmessage)
$mailmessage.dispose()

Notes:

You will need to replace the values in some of the variables above to allow it to work in your environment (ie. SmtpClient.Host, FromAddress, Subject, Body text, Reply to address, attachment path).

You will also need to ensure that whatever machine you are running this script on is "authorised" to send with the SMTP server you have configured.

The final line of code $mailmessage.dispose() is very important when sending emails with attachments. If this line is not included, Powershell 'locks' the file(s) you attached after the message has been sent and will not 'release' them until the Powershell instance you are running is closed.