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In the Send From Other E-mail Address window, click From, change the address book to the global address list (GAL), and then select the user to whose mailbox you were granted Send As permissions. To get similar functionality for POP3 and IMAP accounts see this guide instead. In the new email message in Outlook, click From, and then click Other Email Address. In addition, note that it is an Exchange account feature. It could get filtered out by Junk Email Filters. We use Outlook cloud Exchange and the Office 365 Suite. By default, it doesn’t reply to people outside of your organization. I had found that there was a hidden rule in the Outlook OWA that was forwarding incoming emails to her deleted folder - I deleted the rule, reset her password, and locked her sign in abilities from the 365 admin for a short period of time The user's account had recently been compromised. My boss is suggesting I should create her a new account all together, but for me that's very last resort. I had been doing some reading on the issue, and I'm lead to believe that the user's address has been blacklisted.
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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. Choose Internet option from the drop down menu and click Next. So click the New Send Connector option in actions pane to add. By default, there is no any send connectors configured.
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Your message couldn't be delivered because you weren't recognized as a valid sender. Send Connectors in Hub Transport Server are used to send mail out on the Internet to domains like gmail, hotmail, and so on. She receives this message after sending to an external user: MailTips alerts can be triggered by actions including clicking Reply All to a large recipient list, sending sensitive information to someone outside your organization, or sending a message to someone who is out of office. I have a user who is unable to send emails to external email accounts. Outlook includes MailTips, which help you avoid common, but potentially costly or embarrassing, mistakes.