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I need immediate help. Too many dropped calls after being escalated to next level support.

Stevo Heller 0 Reputation points
2026-03-09T21:31:52.9133333+00:00

Frustrated. I've been on hold now for over an HOUR. And I've been trying to get these Outlook issues fixed for over 3 months. I've waisted countless hours on hold, talking to 1st level support "troubleshooting" until I get this escalated. The last two times ive been able to speak and grant QUICK ASSIST I had the tech drop the call and then closed the ticket. Then another 4 hour attempt to get these issues fixed. On Friday last week I spoke only to a first level tech and he said I would get a call back within 48 hours. 48 HOURS? Then this past sunday I get a call from microsoft at 6:30 a.m. while still in bed. I asked this tech to please give me some time and call my back within two hours. NO CALLBACK! New Ticket request today and I am still on hold 1:22: minutes and counting. And there have been 10+ tickets that have been created for this specific issue.

The lack of customer service is astounding. Is there anything else I can do?

Moved from: Microsoft 365 and Office | Other

Microsoft 365 and Office | Subscription, account, billing | For business | Windows
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  1. Stevo Heller 0 Reputation points
    2026-03-12T23:17:39.1833333+00:00

    OUTLOOK SYNCHING PROBLEM

    I have a Dell Laptop, iPhone 16 and an iPad. I am lost. I cannot seem to get the help I need.

    The issue I started having was that on May 21, 2024. I was unable to send or receive emails and the sub-folders were not synching. After multiple session, eventually the issue was fixed. Then it happened again this past August 2025. Outlook on my laptop was not receiving or able to send emails. Frozen. As was Calendar, Contacts, Mail and notes. My Apple devices were able to stay up to date on each of my devices but would not synchronize with the laptop. My many folders in Mail stopped appearing. Trying to re-populate the IMAP folders wasn’t functional.

    CALENDAR Appointments made in Calendar on Laptop will not synch with IPAD or IPHONE. And appointments made on iPhone or iPad do not show on laptop. Changes made in Calendar reminder times will not work. I cannot set a time different from the default time. Also, when I delete a message from my inbox on my iPhone, it does delete in on my laptop. And when I delete an email from my laptop, it will delete it from Apple devices. They don’t synch. WHEN I MINIMIZE OUTLOOK IT CLOSES the window. IMAP Folders in Outlook are not synching. Query button doesn’t list subscribed folders. When making an appointment I am unable to enter the time of appointment. If I enter a start time of 12:00 p.m. it immediately reverts back to the default time of 8:00.

    I have tried repeatedly to contact support for the past months and have been able to speak to initial tech support. In each of these instances I asked to have this escalated. I have been told and promised that I would get a phone call between 24-28 hours. I have had over 11 instances (each requiring me to stay close to my laptop waiting for the call). I’ve had at least 6 of those callbacks end in mid-fix with a dropped call, a hang-up or “other” problems with your tech support staff. I then would have to go through this ridiculous exercise again, costing me more time waiting than your support staff fixing anything. I have had to repeat my issues every time. Over the past two weeks every single request for escalation failed.

    Service requests

    Calendars and Contact not syncing(#7099310809)

    Service request opened•

    3/10/2026 at 12:11 PM

    Outlook.com issues

    Calendar not syncing along with mailbox and many more(#7099253743)

    Service request closed•

    3/9/2026 at 02:33 PM

    Outlook.com issues(#7099252077)

    Service request closed•

    3/9/2026 at 02:02 PM

    Outlook.com issues(#7099243226)

    Service request closed•

    3/9/2026 at 11:35 AM

    Outlook.com issues(#7099083469)

    Service request closed•

    3/6/2026 at 01:21 PM

    Outlook.com issues(#7098644297)

    Service request closed•

    2/27/2026 at 01:06 PM

    Outlook.com issues(#7098644010)

    Service request closed•

    2/27/2026 at 01:00 PM

    Outlook.com issues

    3 Disconnected assist calls and no callback-Outlook Issues happening for months (#7096828767)

    Service request closed•

    1/29/2026 at 01:48 PM

    3 Disconnected assist calls and no callback-Outlook Issues happening for months

    Recurring issues in Outlook(#7096824829)

    Service request closed•

    1/29/2026 at 12:33 PM

    Recurring issues in Outlook

    7093755377 need technical team(#7096763594)

    Service request closed•

    1/28/2026 at 03:37 PM

    7093755377 need technical team

    Continuing issues with MS Outlook(#7096755377)

    Service request closed•

    1/28/2026 at 12:50 PM

    Continuing issues with MS Outlook

    Need tech support. I've lost all emails, folders and synching(#7093323688)

    Service request closed•

    12/11/2025 at 01:18 PM

    Need tech support. I've lost all emails, folders and synching

    Unable to send or receive email(#7089051732)

    Service request closed•

    10/14/2025 at 05:31 PM

    Unable to send or receive email

    Fix problems importing contacts in to Microsoft Outlook(#7048872028)

    Service request closed•

    8/15/2024 at 11:39 AM

    Fix problems importing contacts in to Microsoft Outlook.

    I need to speak to a supervisor.

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  2. AlexDN 11,065 Reputation points Microsoft External Staff Moderator
    2026-03-10T05:45:08.93+00:00

    Dear @Stevo Heller,
    Thank you for posting your question in the Microsoft Q&A forum. I’m really sorry you’ve had to go through this. From what you described, you have spent many hours waiting on support calls. You have had to explain the same Outlook issue multiple times. You were escalated, but the calls dropped or the ticket was closed before the issue was resolved. You were told to expect callbacks that did not happen.
    I want to reassure you that your concerns are understood. Anyone in your situation would feel upset and worn down after these many attempts.
    To help us guide you more effectively, could you please share:

    • Which support channel have you primarily been using (phone support, chat support, Microsoft 365 Admin Center, or another channel)?
    • Is this related to a work or school account, or a personal Microsoft account?
    • Do you have one active or most recent support ticket number that we can focus on? Could you please provide your ticket number via Private message as picture below: User's image

    Your detailed response will help us diagnose and investigate the issue more efficiently.

    I truly appreciate your patience and understanding. If I misunderstood what you’re looking for, feel free to let me know or share a screenshot. I’d be happy to help further!

    I'm looking forward for your reply. Thank you for your cooperation.

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