Hi @Lindsey S,
Thank you for taking the time to share a screenshot and explain your workflow clearly.
Based on the details you shared, when you compose a new message in Outlook on the web and start typing names in the To field, Outlook does not auto populate or suggest your coworkers even though you have emailed them before.
In Outlook on the web, recipient suggestions are generated by the Microsoft 365 service using a mix of your personal contacts, your organization’s directory (Global Address List), and addresses you have previously used when sending messages. As a result, suggestions may not appear if directory lookup requires additional characters to start searching in a large address list, or if the account’s suggested people data has been reset or adjusted by privacy settings.
Below are some workable options that might be the most appropriate for your current situation:
1/ Use the directory picker to add recipients and confirm directory search behavior
- Open Outlook on the web and start a new message.
- Select the To button to open the Add recipients window, then choose the Global Address List or the appropriate contact list.
- In Search this list of contacts, type a few more characters of the person’s first name, last name, or email address to trigger results, which is expected when the directory is large.
- Select the correct recipient, then select Save to place the address into the message.
2/ Reset the account’s contact search index so suggestions can rebuild
- Sign in to Settings and Privacy with the same work account you use in Outlook on the web.
- Select the Privacy tab, then under Data options expand Manage Contact Search.
- Select Reset Index to rebuild suggested people and contact search signals for your account.
- In the same area, confirm capture of implicit contacts and contact ranking from communications is enabled, because disabling it can reduce suggestions built from prior email activity.
3/ Rebuild recipient suggestions by selecting the person from the directory and sending a short test message
- Add the recipient using the To button directory picker (rather than typing only in the To field), then save the recipient into the draft.
- Send a brief test email to that recipient so the service can re learn the address for future suggestions.
- Then start a new message and type the same name again to check whether the suggestions list is now appearing.
For reference, Microsoft’s guidance on how suggested recipients work and how to add recipients through the address book is available here: Manage suggested recipients in the To, Cc, and Bcc fields in Outlook.
I hope this response has helped address your question and clarify the behavior you're experiencing. Please feel free to reply if you have any further questions, I would be happy to assist further.
Thank you for your patience and your understanding. I look forward to continuing the conversation.
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