Recent Discussions
Outlook Desktop / Send emails via Non-Default Account
Hi, How to make non-default account to appear automatically in From field then external application is composing new email. Have 2 account in Outlook Desktop 365: test1 [@] contoso [.] com - default test2shared [@] contoso [.] com - shared non-default mailbox Option "Always use the default account when composing new messages" is unchecked already. How to make test2shared account to appear automatically in From field without selecting it in drop down list every time we compose a new email or external application is composing new email.
Emails Showing with Black backgrounds while NOT in dark mode?
New to the discussion forum but couldn't find anything about this online that wasn't years old already. We're using new outlook and there are emails that we've been getting (both tests of our own email campaigns and outside emails) that have been forced to use a black background regardless if it's on light/dark mode. It's odd and our emails aren't showing up correctly. If there is a way to fix it - would love to know. They only seem to appear correctly in the web browser version of outlook. I'm looking into ways to force our emails to show up the same in both light and dark mode but thought I'd ask if there was a fix just in case.
Support for auto-filing sent emails
I am looking for a solution to this scenario in the New Outlook: I send tens of emails per day The sent emails are stored in the Sent Items folder I need to manually move each of them into the sub-folders in my Archive folder - e.g. one for support cases Is there any way to automate the step (3) - i.e. to automatically file the sent emails into the folders they belong to? The Classic Outlook had "When replying to a message that is not in the Inbox, save the reply in the same folder" which is not present in the New Outlook. Maybe the New Outlook should have something even more powerful? In addition to this feature, a button suggesting into which folder each message should be filed? Finally, the Outlook Rules are very powerful but they do not apply to the sent emails. Maybe time to generalize these?
outlook contacts continuously restore themselves
I decided to clean out my contacts in outlook, so I exported them all out to a .csv file and then I deleted all 1,200 of them (100 at a time, because apparently microsoft feels that any higher amount would be bad...). Then I spent a few hours in excel combining, consolidating and deleting them down into about 600 contacts. When I went back into outlook and clicked on people, to my surprise all 1,200 of my original contacts were right there again as if I'd done nothing. I figured that some other device must be restoring (through some normal synching process), so I turned off **REMOVED** computers and phones that I've ever used to access outlook). Then I deleted all of the contacts once more, this time using the OWA webpage with my local outlook completely closed. Unfortunately, the exact same thing happens. After repeating that process several more times last night, I shut down my laptop and went to bed. I got up this morning, opened my local outlook app, clicked on people and there were no contacts there at all. For about 5 seconds I was happy, until all 1,200 of them instantly popped right back up like a really bad joke or a dream. Something either on my computer or (I suspect) on microsoft outlook servers is automatically forcing a complete restore of all my contacts. Two side notes: 1) I can create/add and delete single contacts and those changes seem to stick, and 2) I can delete all contacts except a single one and that seems to stick, and 3) I can import my cleaned up .csv file containing 600 contacts back into outlook (with only the one single remaining contact in there), it says that all 600 contacts have been successfully imported, and then within minutes - all 1,200 contacts are back right where they were in the beginning. The truly frustrating part about this issue (and most companies these days), is that IF the customers could possibly **REMOVED** about it so that we can simply continue to make and sell more stuff. It's very sad
Outlook for Mac (Paid Version) – Dozens of Challenges, Any Suggestions?
I don’t think I need to repeat what most of us already know: Microsoft’s in-app Outlook support is incompetent at best, misleading at worst. And so are all other Microsoft channels one can tap in to for support. The so-called “experts” loop the same scripted answers, suggest fixes that cause new problems, or simply stop replying. Tickets are closed prematurely (likely KPI-driven) without solutions, or left hanging with “we’re still working on it” updates every few weeks. My oldest ticket like this is now in month 4. Outlook for Mac feels like a paid beta test, and we are the paying beta testers. My Mistake (Following Bad Advice) On the advice of an in-app “expert,” I moved from Classic Outlook to the New Outlook after my IMAP accounts started duplicating files (Title-of-File 28 and so on). When the New Outlook began breaking down too, I tried switching back. That’s when I lost: My entire address book All reminders Other important data Now I’m stuck in New Outlook, with Classic no longer an option without risking more loss. Where I Am Now I’ve raised a dozen+ tickets and used the in-app support multiple times (currently broken in my Outllook since months). Each time, I asked for a real Mac Outlook expert or higher-level support. Instead, I’ve ended up with a list of about two dozen bugs and broken features (which I’ll share separately). I even sent this list with a letter requesting a real expert and a level-two support person. The result? A kind but non-expert agent. I ticked the box for email contact (which always results in a phone call), then they want screen sharing, then they offer useless answers, show they did not read thoroughly… and the loop begins again. My Main Question Right now, my top priority is: How can I safely revert back to Classic Outlook without losing data? I need a reliable way to back up everything in New Outlook first, so I can restore if things go wrong. The backup option in New Outlook is greyed out. When I asked support, their advice was literally: “Switch back to Classic and make the backup there.” I know… After months of tickets, I still don’t have a safe, confirmed backup/restore method. Why I’m Posting Here I no longer trust Microsoft’s “experts.” And I won’t experiment blindly with their suggestions until I know I can restore my data safely. So I’m asking this community: Has anyone successfully reverted from New Outlook to Classic without losing data? And how did you do this? How did you back up first? Are there tested workarounds for these problems, or is the only realistic option to abandon Outlook for Mac entirely? Any tested, real-world advice would be much appreciated. Thanks. PS and yes, I am on the latest Mac OS and Outlook version. Here is the doc submitted to MS: Subject: Escalation Request – Outlook for Mac Issues Dear Microsoft Support, First, I kindly request that this case be assigned to an agent with full Outlook for Mac expertise. So far, most of the agents I have spoken/dealt with seem more Windows-focused or not fully trained in Outlook for Mac. Important Notes Before Troubleshooting Pleasedo not suggest reinstalling Outlook or switching back to Legacy without addressing the risks outlined below. I havenine IMAP accounts (no POP accounts). When I previously followed support advice to create a new identity and reinstall Outlook, I lost all reminders and address book entries. I only managed to recover them by restoring from Time-Machine. This was unacceptable and must not happen again. If reverting to Legacy is necessary, I need aclear guarantee that no emails, reminders, or contacts will be lost. The reason I initially left Legacy was because of persistent folder duplication (e.g., folders named xx17 and higher) and your agent said this would be a good solution. Unless there is a permanent fix for this, reverting is not a viable option. Enclosure: Detailed Issue List – Outlook for Mac (Office 365, Commercial) A. Data Loss Risks & Backup # Issue Description Requested Fix Severity 1 Returning to Legacy Reverting risks data loss (reminders, contacts, calendar). Legacy also created random duplicate folders (xx17, xx18, etc.). Guarantee safe revert without data loss or folder duplication. High 2 Backups Export/backup option is permanently greyed out. Legacy allowed full backup. Enable backup/export for accounts, reminders, contacts, etc. High B. Search & Synchronization # Issue Description Requested Fix Severity 3 Search Failures (Visible Emails) Search fails to locate emails that are clearly present. Fix search reliability. High 4 Search Failures (Disappearing Emails) Emails vanish from search though retrievable via a deep search in UBF8T346G9.Office folder. Ensure Outlook search indexes all mail consistently. High 5 Reply/Sending Failures - Some messages stuck as “downloading” - Some messages hang in Outbox and can’t be deleted. Fix sending/reply bugs and allow removal of stuck messages. High 6 Duplicate IMAP Folders Some IMAP accounts show extra Inbox or Archive folders. Clarify origin and safe removal. Medium C. Email Functionality & UI # Issue Description Requested Fix Severity 7 Viewing Replies Legacy showed sent replies via a button; grouping in new Outlook is inconsistent. Restore a reliable way to view replies. Medium 8 Incorrect Sent Mail Count Unified Sent box shows “4,294,967,295” messages. Correct message count. Low 9 Replies Disappearing Some email replies disappear entirely unless found via deep file search (see 4). Prevent loss of replies. High 10 Attachment Indicator Emails with attachments no longer visually marked. Reintroduce indicator. Low 11 Outbox Editing Emails in Outbox cannot be opened/edited offline. Restore editing functionality. Medium 12 Categories Greyed Out Categories unavailable for IMAP inbox emails. Enable categories for IMAP. Medium 13 Trash Behavior Some emails vanish immediately after moving to Trash. Keep items until manually deleted. Medium 14 Restoring Deleted Emails Cannot drag emails from Trash back to Inbox. Allow restoring deleted items via drag/drop. Medium D. Calendar, Contacts & Reminders # Issue Description Requested Fix Severity 15 Teams Meeting Reminders Meeting reminders lack join links; accepted invites sometimes show as unconfirmed. Restore full functionality of Teams invites/reminders. Medium 16 AppleScript Support Commands like IMAP and Account appear in dictionary but don’t work. Restore full AppleScript functionality. Medium 17 Contact Autofill Stored names don’t appear in search/autofill. Fix contact lookup. Medium 18 Duplicate Contacts Contacts duplicate sometimes automatically; removal must be manual. Provide bulk de-duplication or stop auto-duplication. Medium 19 Duplicate Reminders Reminders duplicate sometimes automatically, removal must be manual. Provide bulk de-duplication or stop auto-duplication. Medium 20 Contacts Toolbar Cannot customize toolbar in Contacts. Enable customization. Low 21 Adding Contacts Cannot add email address to contacts by clicking it (was possible in Legacy). Restore this feature. Medium 22 Calendar Conversion Legacy allowed emails to be converted to calendar entries. Restore feature. Low 23 Calendar Invites Invites not available unless sent to primary account. Support invites across all accounts. Medium E. Notifications, Updates & Misc. # Issue Description Requested Fix Severity 24 In-app Support Not Working In-app Outlook support is non-functional and has not provided useful responses. Confirm why it fails and provide a working alternative. Medium 25 Support Notifications Daily pop-up about “Customer Support activity,” even when none exists. Feature now broken. Stop or fix notification. Low 26 Frequent Update Pop-ups Update window appears too often. Allow disabling or limiting update prompts. Low F. Support Experience & Compensation # Issue Description Requested Fix Severity 27 Support Experience Agents missed appointments, gave copy-paste answers, and closed unresolved cases. Improve continuity, assign competent Mac agent, ensure accountability. High 28 Compensation Request More than 20 hours lost on missed calls, repeated troubleshooting, and unproductive sessions. Confirm process for requesting compensation for lost time and effort. See below. High Request for Resolution and Compensation Given the number and persistence of these issues, Outlook for Mac (Commercial) feels under-tested and unstable despite being a paid product. I have already spent more than 20 hours waiting for promised calls, writing follow-up emails, dealing with answers that regress, non-Mac trained agents, bad copy-paste answers, attempts by agents to close unresolved issue, and troubleshooting without resolution to name a few. I feel like an unpaid and poorly treated beta tester! I request: Escalation to an Outlook for Mac expert. Clear guidance on safe backup/recovery for contacts, reminders, and accounts. A statement on how I can requestcompensation for this buggy application, the time spend and the ongoing headaches it gives, to name a few. Maybe the easiest is to cancel the need to pay the licencing fees. Please confirm the appropriate channel for submitting this claim unless you are authorised to so immediately, which I hope for simplicity’s sake you are. Thank you for your attention. I look forward to your prompt and constructive response.
Mobile app Sub folder notifications
We have pushed all our users to use Outlook mobile apps on iOS and Android, however many are complaining that they have created rules on the Outlook desktop client to put emails in certain sub folders (i.e. all emails from my manager go into a sub folder) and not getting notifications. As the email is moved to the folder before it gets to the client, the mobile apps do not display a notification. As a work around I've had to set up some Flows so that if email received from a certain email address, it displays a notification. The user can then open Outlook and go to the relevant folder. Its not pretty. This seems like a basic feature, its available in the iOS and Android stock mail apps which most used before we pushed them to Outlook. Any plans on the mobile apps to have notifications for sub folders?A 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.Constantly being asked to reauthenticate accounts in Outlook for Mac
Hey everyone, I started running into a strange issue a few days ago. I am using Outlook for Mac Version 16.102.1 (25101829) with seven accounts configured. Out of nowhere, I keep getting repeated prompts to reauthenticate all my accounts. I use the Microsoft Authenticator app on my iPhone, get the push notification, approve the two digit code, and everything goes through fine. A few hours later, Outlook shows the same pop up again asking me to reauthenticate. I have gone through this process at least ten times now, and it keeps happening. Is anyone else seeing this issue or found a fix?Help exporting 1000+ contacts
Hello and thank you in advance, I have a list of 1000+ email addresses. i need to export the full contact info for them from the global address list to a CSV file ( need title and department field specifically). These emails are not currently in my personal contacts. Is there a way to do this quickly, without manually searching up each email and adding it to my contacts? I tried pasting the email addresses into a contact group and saving it as a text file, but that only pulled in the contacts name. Is there a way I can either: A: Quickly add 1000+ emails to my contacts from the global address list? or B: export the contacts directly from the GAL? Thank you again for your help!
webcal links not opening correctly in outlook
I create a webpage with the following content <a href="webcal://www.mydomain.se/mycal">TEST</A> When I click the link, outlook opens and tries to add a calendar, but sets the URL to //www.mydomain.se/mycal It also complains my url is incorrect. I would have expected it to insert a link like https://www.mydomain.se/mycal Is this an issue with outlook, or am I doing something wrong? Changing the link into <a href="webcal:https://www.mydomain.se/mycal">TEST</A> will make it work. But this seems like an incorrect url and might break other integrations, I guess. Any ideas?New Outlook Opening in Edge Browser after updating last week
I am currently running Windows 11 Insider Preview Build 25951-230908-1539. I am also running the new outlook which I installed by using the toggle switch in the "legacy" outlook. I did an update either last week or the week before of the new outlook when prompted and since I did that the new outlook does not open up in the native app anymore it keeps looking like it wants to but then it opens up a new tab in the Edge browser and opens up in there. I tried going into the settings on Windows and doing a repair and a reset but neither of these options helped. I figured that since it was just going to be a web app wrapped to look like an app I would install it that way through the browser, but I decided to test it correctly, I undid all of that and waited to see if another canary update or outlook update would fix it, but just tried it again this morning 9-25 and still same issue happening. Any thoughts? Thanks SteveMicrosoft Outlook Credential Popup Hidden / Blank on Entra ID–Joined Devices
Hello Community, I am encountering a persistent issue with Microsoft Outlook on Entra ID (Azure AD)–joined devices. Users are repeatedly prompted for credentials, but the popup does not display properly — it appears as a tiny, mostly blank window (see attached screenshot) and is sometimes only visible in Task Manager. As a result, users cannot complete the login process. Environment & Observations: -Devices are fully Entra ID joined. -Users have valid Microsoft 365 licenses. -The popup appears as a small, blank, non-interactive window. -Clearing cached credentials and re-registering Microsoft Accounts / WAM components did not resolve the issue. -Registry value WamDefaultSet shows YES. -More common on fully Azure AD–joined devices Troubleshooting Steps Already Attempted: -Cleared cached credentials in Windows Credential Manager. -Re-registered Microsoft Account / WAM components. -Verified user accounts and M365 license assignments. -Checked network connectivity and device compliance. Questions / Guidance Requested: Is this a known issue with Outlook credential popups on Entra ID–joined devices? Are there registry tweaks, Intune policies, or configuration changes that can ensure the popup renders correctly? Could this be related to Conditional Access, SSO, or token handling in Entra ID? Any insights or solutions would be greatly appreciated.Outlook does not recognize language in E-Mail automatically
Since I have Windows 11 I have been having all kinds of problems with Outlook - from installing my e-mail accounts to getting language settings to work. I have tried using co-pilot to help me with this - it's been completely useless, as it seems to access only outdated info or points me in completely wrong directions. so I hope and appreciate that a real human being (three yeahs for you!!) can help me with the following: even though I have installed all my required language packs and set that it should automatically notice the language I am writing in, it fails to do so since my update. What is going on there? thanks a bunch for your assistance! ManuelOutlook search not working properly
Hello all I just pourchased a new laptop and using classic outlook with micrsoft 365 windows 11. Our emails are hosted on gmail and we have synced everything over with both GWSMO and now with imap. for some reason when i use outlooks quick search it only displays results form subject and not from the body of the email. We have literally tried everything including rebuolding the index etc., I dont want to use new outlook as it doesnt have certain features like schedule send etc. anyone have any suggestions on how to get classic to search properly
Recent Blogs
- As technology moves forward, so do the ways we communicate. The world is rapidly changing with cloud computing, hybrid ways of working, and generative AI. To keep up with all these changes, Outlook i...Jun 24, 2025
- Since its launch, Copilot in Outlook has helped you manage and triage your email, providing drafting assistance, summaries, and insights to help you save time. Whether you need help drafting the appr...Nov 19, 2024
