Drag and drop email-to-task (To Do) from favourites bug
It's been driving me crazy but I finally seemed to figure out why I could no longer drag emails into the ToDo pane to create tasks. Firstly, it seems that you can only drag emails to create tasks for business, or non-Microsoft accounts, I'm not sure which, or both. Secondly, you need to select an email from within the actual account in the left pane, NOT favourites. See this image: https://imgur.com/a/ZdyAvYb This bug may have been introduced in the last few months, as I don't recall encountering any issues until somewhat recently. Anyway, I hope this helps prevent someone from ripping out their hair like I was.
New Outlook Data Classification/DLP/missing features
Hello, I am noticing a couple of new issues with New Outlook. All the above works with old Outlook. -Auto Labelling not working(Based on Sensitive info type). -Label requirement not working (i.e. Users can send without a label, in old OLK/OWA, they get a prompt to label the email) -Label Inheritance not working (from attachment) -Smime Signing/Viewing emails. -If you set a dlp policy with an option to add certain label based on a detected sensitive info type on unlabelled emails, The policy tip is displayed but the label is not added. All the above works with old Outlook and most work in OWA but all the above does not work in New Outlook. Any workarounds? are those functions not supported yet? Any help will be appreciated.
New Outlook: Shadow contacts not stored in Outlook.com, no sync/export and missing Birthday calendar
I’m reporting a reproducible data‑integrity issue in the New Outlook for Windows that affects Outlook.com contact storage and synchronization. 🔍 Summary When a contact is created in the New Outlook, the client appears to save it successfully. However, the resulting contact is not stored in the user’s Outlook.com account as a normal cloud contact. Instead, it becomes what I would describe as a local “shadow contact” in the New Outlook cache. ⚠️ Observable Behavior • The contact appears in Outlook.com → People, but does not show “Stored in: Outlook” • The contact does not appear in Outlook.com CSV exports • The contact does not sync to mobile devices connected to the same account • The contact does not populate the Outlook.com Birthday calendar • The contact is lost if the New Outlook app is reinstalled or its local store is cleared 🧪 Steps to Reproduce 1. Open the New Outlook for Windows 2. Create a new contact and add a birthday 3. Save the contact 4. Open Outlook.com → People 5. Locate the contact — it will appear, but the “Stored in: Outlook” field is missing 6. Export contacts from Outlook.com (CSV) — the contact will not be present 7. Check a mobile device configured with the same Microsoft account — the contact will not be present 8. Check the Outlook.com Birthday calendar — the birthday will not appear 9. Reinstall the New Outlook app — the contact will be gone ✅ Expected Behavior • Contacts created in the New Outlook should be stored as first‑class Outlook.com contacts • They should appear with a proper “Stored in: Outlook” location • They should sync across devices, export via Outlook.com, and populate the Birthday calendar ❌ Actual Behavior • Contacts created in the New Outlook are effectively “shadow contacts” stored in a local cache • They look normal in the New Outlook UI, but they are incomplete, non‑synchronizing objects from the service’s perspective 📉 Impact • Silent data loss risk for users who assume contacts are in Outlook.com when they are not • Inconsistent contact and birthday data across devices and services • Split contact store model: • Real Outlook.com contacts • Local shadow contacts created by New Outlook 📎 What I’ve Already Done • Submitted feedback through the New Outlook (Help → Feedback → Report a Problem) • Submitted a detailed report via the Windows Feedback Hub • Contacted Microsoft Support, who advised that escalation must occur via Feedback 📣 Request I’m posting this here to document the issue publicly and to ask: • Can anyone from the Outlook / Exchange / Outlook.com team confirm this behavior? • Can other users reproduce this with the steps above? Given the data‑integrity implications, I’m hoping this can be brought to the attention of the relevant engineering team. Any confirmation, additional data points, or official guidance would be appreciated.New Outlook: Creating Rules for CC: and Sent Items (Workaround solution)
Many users have said they miss one of Outlook Classic's features: the ability to create rules for sent items. One popular use is automatically moving a Sent item to a designated folder, reducing the time it takes to handle email. Currently, rules in New Outlook manage received messages in the Inbox. This blog provides details. New Outlook Limitations: Outgoing Message Rules » TRACCreations4E I am happy to share that I have finally come up with a workaround to add a copy of the message you sent to a folder of your choice. Yes, the original message will remain in the Sent folder, but you don't have to move it manually. This method should hold you over until Microsoft rolls out the functionality for "Sent rules," which has not been added to the roadmap. Watch the full tutorial to discover how you can: Setup your email Use hashtags in your signature line Set up an automatic rule Blog Post: New Outlook Sent Email Rules: Here’s the Workaround Video: https://youtu.be/guOjz5lHJEY?si=un6jp2afgO-3PAhg Remember, this is a workaround solution. I am also waiting patiently for the Sent Rules functionality. If you find this information helpful, please mark it as the best response to assist others with the same question. /Teresa #traccreations4e 6/11/2024Significant changes to the New Outlook Calendar Event User Interface
In October 2025, the New Outlook Calendar Event was redesigned to incorporate Copilot, leading to a complete user interface makeover. Many icons were rearranged. This blog post includes a screenshot, icon placement, and descriptions. New Outlook Scheduling Gets a Makeover - Copilot Chat Joins #traccreations4e-p25 10/29/2025Outlook Offline Phase I: Available Features
Updated November 18, 2025. The following are some of the key features introduced in Outlook Offline Phase I: Offline Email Access: Users can read, reply to, and compose new emails offline. These actions will be synchronized once the user reconnects to the Internet. Calendar Management: Users can create, edit, and delete calendar events while offline.. Contact Access: Access to contacts is available offline, allowing users to look up contact information. Synchronization: Any offline changes, such as sending emails, updating calendar events, or modifying contact information, will automatically synchronize once the internet connection is restored. Unsupported Features While Outlook Offline Phase I brings a host of new functionalities, it is important to note that not all features are supported in the offline mode - yet. I recommend downloading the updated list of supported and unsupported features to ensure you have the most up-to-date information on what is supported and what is not. Video: https://youtu.be/qzHfnlfhuEw Visit Website: Microsoft Outlook's Offline: Features Availability » TRACCreations4EA major step backwards: Classic Outlook vs. New Outlook on changing the "From" sending account
The Issue: In New Outlook, changing the "From" address after you have already started composing an email message opens a new, blank message window, forcing you to copy and paste your original message subject, contents, and attachments. This is an irritating change from Classic Outlook, where you could simply switch the sending account from a dropdown menu while keeping your drafted message fully intact. Expected behavior: When changing the "From" address while composing a mail message, it should simply be updated to the newly selected account, and the body, subject line, and any attachments of the message you are writing at that time should be preserved within the same composition window. The Classic Outlook Way (The Right Way) to Switch the "From" address: For years, my workflow in Classic Outlook has been simple. I click "New Email." The new message window opens, and the "From" field shows the currently selected account. I start writing my message. Then I realize I wanted to send it from another mail account. I click the "From" button, and a dropdown menu appears with all my accounts. I pick the one I want, and I'm good to go. The message content is untouched, it's all still there. Changing the From-address is a two-second action that is intuitive and efficient. The "New Outlook" Way (The Baffling Way) to Switch the "From" address: Now, I try to do the exact same thing in the "New Outlook." I click "New Email." The new message window opens, and the "From" field shows the currently selected account. I start writing my message. Then I realize I wanted to send it from another mail account. I click the "From" button, and a dropdown menu appears with all my accounts. I pick the one I want. But then, after choosing a different From-address, a completely blank new message is opened. And I have to copy/paste everything from the message window I was writing in before to the newly opened message window. So annoying! This feels like a classic case of simplifying the UI to the point where it loses critical functionality. What used to be a simple dropdown selection in Classic Outlook is now an irritating multi-step process in New Outlook. It seems to be an intentional design choice, but it's one that ignores the reality of how users with multiple mail accounts actually work.
New Outlook not playing new email sound or sending notifications.
I'm using the New Outlook and it's not playing the new email sound and not displaying notifications for new emails. If I switch to the Classic Outlook it plays the sound and sends a notification. I have checked all the sound and notification settings, all updates are installed and I'm running the latest version. How do I fix the issue of the New Outlook not playing the new email sound and not displaying a notification?New Outlook: Users Say It's Broken—Microsoft response.
I had the opportunity to interview Caitlin Hart, the Principal Product Manager for New Outlook, where I asked the challenging questions of frustrated New Outlook users, IT Consultants, and IT developers. We talked about: Is the New Outlook just a wrapper for the web version? Why didn’t Microsoft recreate Classic Outlook from scratch? Why are users forced to switch to the New Outlook app? Why are some users still resistant to adopting the New Outlook? When will New Outlook meet the needs of power users? How is Microsoft encouraging VBA developers to stay ahead? And more Watch the video for Caitlin's responses. Video: https://youtu.be/5WYjmzrOZI8 #traccreations4e-p25 4/26/2025
