Two Linked Outlook Issues Causing Accidental Emails to Wrong Clients Feature Request + Bug Report
Hi Outlook Community, I'm posting this after a real incident at work where I accidentally sent a confidential email to the wrong client. After reflecting on what went wrong, I've identified two separate but related Outlook issues that compounded the mistake and I want to raise both here so they reach the right people. Bug: Autocomplete Recipient Changes After You Press Enter This one is subtle but dangerous. When you start typing a name in the To/CC/BCC field, Outlook shows an initial autocomplete suggestion. If you press Enter before the search fully resolves, the dropdown refreshes mid-selection and the contact that actually gets added is *different* from the one that was highlighted when you hit Enter. You don't get any warning. You believe you've selected the right person. You haven't. I've submitted this via the Feedback Portal here: https://feedbackportal.microsoft.com/feedback/idea/9a32197e-5424-f111-9730-0022485314bc Suggested fix: Freeze the highlighted contact reference at the moment Enter/Tab is pressed, independent of any ongoing background search refresh. --- Feature Request: Cross-Domain Recipient Warning (like the missing-attachment check) Outlook already warns you before sending if it detects you may have forgotten an attachment. I'd love to see a similar pre-send check for this scenario: You are about to send an email to recipients across 3 different organisations. Did you mean to do this? In consulting, legal, finance, and any client-facing role, it's very easy to accidentally include someone from Client B on an email meant only for Client A especially when contacts share similar names. A configurable domain-count threshold (default: 2 external domains) with a soft confirmation prompt would catch this class of mistake before it becomes a compliance incident. Key asks: - Configurable threshold (user-level) - Domain whitelist support (e.g., always allow your own org + a known partner) - Covers To, CC, and BCC combined - Non-blocking same UX pattern as the attachment warning I've submitted this as a feature request here: https://feedbackportal.microsoft.com/feedback/idea/9a32197e-5424-f111-9730-0022485314bc --- Has anyone else run into either of these? Would love to know if the autocomplete bug is reproducible for others that would help push it up the priority queue. Thanks for reading. Sudharm PIt’s now easier to access iCloud Mail, Calendar, and Contacts in Outlook
We’re excited to announce that the new Outlook for Windows, Outlook for Mac, and Outlook for iOS and Android now support easier iCloud Mail, Calendar, and Contacts access. You no longer need to create and enter app-specific passwords to access your iCloud data in Outlook apps. Now using the OAuth 2.0 authentication protocol, simply sign in with your Apple Account to access your iCloud Mail, Calendar, and Contacts in Outlook. If you already have iCloud set up in Outlook, in the coming months you will be asked to sign in, which will reauthenticate using the new OAuth 2.0 flow. Availability The ability to access iCloud Mail, Calendar, and Contacts using the new authentication flow is rolling out across the new Outlook for Windows, Outlook for Mac, and Outlook for iOS and Android. If you attempt to access iCloud data and are presented with the previous Basic Authentication flow (prompting for an app-specific password), ensure you’ve updated to the latest Outlook app version and restart Outlook. For classic Outlook for Windows users, we recommend trying the new Outlook for Windows, which provides both the new authentication flow and built-in support for iCloud Mail, Calendar, and Contacts without the need for an Outlook add-in. Feedback We would love to hear from you. To submit your feedback, select: Help > Feedback in the new Outlook for Windows and Outlook for Mac Settings > Help & Feedback > Send Feedback in Outlook for iOS and Android
Outlook for Mac enterprise toolbar customization
I'm a Mac systems administrator in an organization that uses a third-party plugin for reporting phishing/spam emails. We are looking for a way to ensure that our reporting button is in the toolbar by default (while still allowing end-user customization) and the default Microsoft one is not in the toolbar by default. I've checked the administrator's guide info here: https://learn.microsoft.com/en-us/microsoft-365-apps/mac/preferences-outlook and while there are ways to customize a LOT of Outlook's features for enterprise purposes, there doesn't seem to be a way to specify a toolbar entry be present or not.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.
Email from “Kenzie Brooks” in my inbox but the email is …
mailto:email address removed for privacy reasons an email address “outlook_6720859FBEB7B349@outlook.c0️⃣m” I cannot reply to the email. I would like to know if anyone knows what/how this person was able to email me with such a bizarre email, yet maintained her name for the header. is this a hack or something more nefarious?Outlook for Mac, 365, Contact List
I have Outlook for Mac, new Outlook, with a Microsoft 365 custom domain account. I wasn't to create a Contact List. I have some addresses that I want to add that are not in my account Contacts. How do I add these names with the the name so when it is add to the list shows as follows: Len Levin xxxxx.domain.com Thanks Len
Outlook for Mac missing ToDo
Since a recent update, our Mac clients don't have any way to view ToDo or Tasks in the New Outlook. The tasks don't show in the My Day/Task pane, nor do we have a ToDo Icon ion the left sidebar like users of New Outlook on Windows do. Accessing OWA is now the only way for users to see tasks/flagged emails, but very much not the preferred solution since there IS a desktop client which should do that. Microsoft® Outlook for Mac Version 16.105 (26011018) This is a serious usability issue, is this really a design decision or some sort of an issue?Attachments to calendar events
I have outlook version 16.106.1 and for some reason the attach file icon is not active. Can I get some advice on how I can activate this so I can add attachments to events I schedule in my calendar. I don't seem to be able to even copy over emails to scheduled events. Any advice appreciated.Mac-Outlook - Attach files to a calendar or an appointment
Hi, I've been using Outlook on Windows for many years. I especially like the calendar with its many functions as a professional tool. In my calendar entries or appointments, I like to save documents that are important for the appointment. E.g. PDFs or Word files. This is possible without any problems under Windows. The documents can simply be dragged into the appointment and I can save any file. This function does not seem to be available in Outlook for Mac. Even with the completely new version from 2021 this does not seem to work. I have already tried to move my entire Windows calendar to the Mac for a test. All calendar entries are fully visible and usable after the move to the Mac! Including the all attachments (PDFs and every other files attached). But I cannot create a new entry with a PDF attachment. Is there a solution to the problem? Am I missing something?
Outlook for Mac - Google Calendar Interop
Hello! We seem to be having a slight issue where we (Google Workspace) and our sister company (Microsoft 365) have set up Calendar Interop using the Microsoft Graph API connector. Current Setup: Calendar Interop is configured to share free/busy time between Google Workspace and Microsoft 365 users. The interop is configured correctly and working as expected across most platforms. Our Issue: Users on the newest version of Outlook for Mac cannot seem to view the Google Workspace calendars correctly. Instead of seeing free/busy time slots, the entire calendar appears fully blocked out (as if all time is marked as busy). Tested already, and confirmed: OWA — works perfectly, free/busy displays correctly Outlook for Mac in Legacy Mode — works perfectly, free/busy displays correctly New Outlook for Mac — entire calendar blocked out This leads me to believe the interop configuration, permissions, and data are all correct. It almost looks like some kind of rendering issue, perhaps a bug, but I cannot be sure. I am also wondering if this has anything to do with any new security on the newer versions of Outlook for Mac? We are using the Graph API connector (not EWS), which is the recommended way for setting up the interop, but still have this issue. Has anyone else experienced this, or is there a known fix or workaround short of reverting to Legacy Mode? Any help or insight would be greatly appreciated. Thanks in advance!
