When sending an email you may get an error about the email address being stale.
This can be due to many reasons including people's email address changing or a change to a contact. Please follow the steps below to fix the issue.
Verify recipient's email address and resend your message in Outlook
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Open the bounce message. In the Report tab, choose Send Again.

If your original message had an attachment larger than 10 MB, the Send Again option might not be available or might not work. Instead, resend the message from your Sent Items folder. For more information, see Resend an email message.
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In the new copy of your message, select the recipient's email address in the To box and then press the Delete key.
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Remove the recipient's email address from the Auto-Complete list (a bad or outdated entry could be causing the problem):
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In the To box, start typing the recipient's email address until it appears in the Auto-Complete drop-down list as shown below.

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Use the Down Arrow key to select the recipient from the Auto-Complete drop-down list and then press the Delete key or choose the Delete icon
to the right of the email address.
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In the To box, continue typing the entire recipient email address. Be sure to spell the address correctly.

- Use the Down Arrow key to select the recipient from the Auto-Complete drop-down list and then press the Delete key or choose the Delete icon to the right of the email address.
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In the To box, continue typing the entire recipient email address. Be sure to spell the address correctly.
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Click Send.