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Add Fixes or workarounds for recent issues in classic Outlook for Windows

Nola Scheid 2025-12-01 06:36:06 +00:00
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Things changed on February 1st, 2024 when Google and Yahoo started applying new email sender standards in an attempt to improve their users’ experience. Even with the correct SMTP details, the server might be down or malfunctioning. Understanding the specific error codes returned by the SMTP server can help diagnose the issue. Mistyped usernames or passwords can prevent successful authentication with your SMTP server, leading to failed email sends. To edit a shared calendar, go online to your own Outlook.com calendar, open Calendar for Windows 10, or use a mobile device. Read how to Add your Outlook.com account to another mail app.
Use the Microsoft 365 setup troubleshooter to install Microsoft 365, Office 2021, Office 2019, or Office 2016 on your Windows PC. This option could be useful if you constantly have to wait for Outlook to rebuild its data file when you restart. There are multiple ways for you to send and receive email, and multiple versions of Outlook available. If the images in these topics don't match what you see on your screen, you might be using a different version of Outlook. If you can't receive new email messages, there are several troubleshooting steps you can take. If you've successfully sent and received email from classic Outlook before, and now Outlook repeatedly asks you to reenter your password, one of two things may have happened.
The built-in Outlook repair tutorial back-off mechanisms in the indexing component of Windows Search or WDS pauses the indexing of Outlook data when the system is under heavy use. The easiest way to let the indexing finish is to leave Outlook running overnight.Additionally, you can reduce performance issues by running Outlook in Cached Exchange Mode. In this mode, Windows Search or WDS searches the local copy of the mailbox instead of the mailbox content on the server. I even reduced mailboxes sizes and that didn't help, I setup a new user (albeit existing PC but new windows profile), and he is having the same issues. If the mailboxes open automatically after removing them and restarting Outlook, they may be auto mapped. This setting can be changed by an Exchange admin by submitting a request via Jira and including the usernames of the client and the usernames of the mailboxes that need to be removed.
Currently, you can't use Outlook on Windows to edit calendars that are shared with your Outlook.com account, even if you've reconnected your Outlook.com account to Outlook. We're working to make it possible to edit shared calendars in Outlook 2016 for Windows. If you manually type in the secondary connected account email address in the "From" field, the email is sent as "On behalf of" your primary Outlook.com account. You can use [Outlook repair tutorial](https://fixoutlookhelp.wordpress.com/2025/10/29/repair-outlook-ost-and-pst-files-2025-guide/) Microsoft Support and Recovery Assistant to diagnose both Calendar and Mail issues that affect Outlook. To download and install the Assistant, see About Microsoft Support and Recovery Assistant. In some cases, an Outlook messaging profile may be misconfigured.
Outlook Live support is the customer service and technical support provided for users of Outlook Live, the online version of Microsoft’s Outlook email and personal information management software. "Outlook support status" generally refers to the current availability and extent of technical Outlook repair tutorial support and customer service provided by Microsoft for its Outlook product line. This can include Outlook.com (the free web-based email service), Outlook as part of Microsoft 365 (formerly Office 365), and the standalone Outlook desktop application available for Windows and macOS.
To reduce the number of items that are stored locally, limit the synchronization window that's used for shared folders. These keys don't clean up older Calendar content that was already downloaded. However, this method can be effective if you're willing to clear offline items and resync your Calendar (instead of bulk deleting old items). If you already have the Calendar in the profile, you have to clear the Offline Items after you set the registry keys and restart Outlook. In Sync Window Settings, adjust the number of months of data that are synced for the primary shared calendars. Use the Turn on shared calendar improvements option for users who have edit permissions to a shared calendar to improve performance.
Sometimes you send an email and discover later that it is not delivered to the intended recipient. By following this checklist, you can systematically troubleshoot and resolve most common email sending issues. If you typically use an Outlook.com account for email, this issue can occur if there are multiple aliases on the account and the 3rd party email address is the primary alias. Customers with only a 3rd party email address set up as the username of their Microsoft Account will be asked to add a 1st party Microsoft alias to their account before accessing Outlook.com.
However, if you want to change your password with your email provider, you'll need to visit their website or help desk, or contact your email administrator. For example, if you have a Yahoo! account, you first have to change your password at Yahoo.com. Once you've changed your password with your email provider, you can update the password in Outlook. See Change or update your email password for more information.