Outlook classic: Tasks issues

Christopher Santomassimo 0 Reputation points
2026-08-10T10:30:09.6866667+00:00

After the August 7 update to M365, in classic Outlook, I can no no longer see attachments to Tasks that I created before the update. I also cannot add attachments to new Tasks. The attachments appear in the Tasks if I view then using the To Do app.

Microsoft 365 and Office | Microsoft To Do | Other
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  1. AI answer

    2026-08-10T10:30:28.91+00:00

    This matches a known classic Outlook bug affecting attachments in tasks when Rich Text formatting is involved. In this condition, the attachment can exist but be effectively invisible in the task window. The paperclip may still appear, and the same task can still show the attachment in the To Do app.

    What is supported from the available guidance:

    1. In classic Outlook, try selecting the tiny invisible placeholder area in the upper corner of the task window.
      • If the attachment is present, clicking that 1-pixel block can open it.
      • This is a workaround, not a fix.
    2. For newly created tasks, the issue is also consistent with the same known bug.
      • A full Online Repair may not resolve it.
      • The reported guidance indicates the issue was recognized and a fix was expected through Outlook updates.
    3. If task access is critical, use the To Do app as a temporary workaround.
      • In classic Outlook, select the To Do icon on the left margin to open the Tasks pane.
      • If preferred, set To Do as the default task experience through File > Options > Tasks > Open tasks in the To Do app.
      • When this option is enabled, opening tasks from the To-Do Bar, Reminders window, or Daily Task List opens them in To Do instead of classic Outlook Tasks.
    4. If assigned tasks are involved, note that tasks assigned from Outlook for Windows must be accepted or declined in Outlook for Windows.
    AI-generated content may be incorrect. Read our transparency notes for more information.

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  2. Jhun Buala 5,715 Reputation points Independent Advisor
    2026-08-10T11:36:37.6466667+00:00

    Hi Christopher,

    Good day. Sorry to hear about this issue. This appears to be a classic outlook regression, where task attachments are still present but are not displayed or manageable in the classic Outlook Task interface. Try these things:

    A. Check your Outlook build.

    1. In classic Outlook, go to File > Office Account.
    2. Note the Update Channel and Version/Build.
    3. Since the problem started immediately after an update, this information is important for identifying the affected build.

    B. Try Outlook in SafeMode.

    1. ress Windows + R.
    2. Enter: outlook.exe /safe
    3. Open an affected Task and see whether the attachments are visible.
    4. If they work in Safe Mode, an Outlook add-in may be interfering.

    C. Test a new Outlook profile

    1. Close Outlook.
    2. Open Control Panel > Mail > Show Profiles > Add.
    3. Create a temporary profile and configure the same account.
    4. Check whether Tasks and attachments work there.

    D. Repair Microsoft 365

    1. Go to Settings > Apps > Installed apps.
    2. Find Microsoft 365.
    3. Select Advanced options/Modify, depending on your installation.
    4. Run Quick Repair first.
    5. If that doesn't help, try Online Repair.

    E. If nothing works, try to roll back the Office update.

    I hope this helps.

    Regards,
    Jhun

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