Many Windows Server administrators encounter situations where scheduled tasks appear configured correctly but fail to trigger at their designated times. The specific case we're examining involves:

• A task set to run daily at 6:50 PM
• Configured to repeat every 10 minutes indefinitely
• Shows correct "Next Run Time" but doesn't actually execute
• Manual execution works fine
• Issue began after disabling/re-enabling the task

Through troubleshooting similar cases, I've found several potential causes:

# Check task status in PowerShell
Get-ScheduledTask -TaskName "YourTaskName" | Get-ScheduledTaskInfo

Sometimes the task cache gets corrupted. Try exporting, deleting, and reimporting:

# Export task
Export-ScheduledTask -TaskName "YourTaskName" -TaskPath "\" -XmlFile "task.xml"

# Delete task
Unregister-ScheduledTask -TaskName "YourTaskName" -Confirm:$false

# Reimport task
Register-ScheduledTask -Xml (Get-Content "task.xml" | Out-String) -TaskName "YourTaskName"

The Windows 2008 Task Scheduler has some quirks with repeating triggers. Try this alternative configuration:

$trigger = New-ScheduledTaskTrigger -Daily -At "6:50PM" 
$trigger.RepetitionInterval = "PT10M"
$trigger.RepetitionDuration = "PT0S" # Infinite duration

Several factors can prevent task execution:

• User account permissions (try running as SYSTEM)
• Power settings preventing wake-from-sleep
• Task history limit reached
• Concurrency settings conflicting

For persistent issues, enable detailed logging:

Windows Registry Editor Version 5.00

[HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion\Schedule\Diagnostics]
"TaskStatusLogging"=dword:00000001

Then check Event Viewer under Applications and Services Logs > Microsoft > Windows > TaskScheduler.

For critical tasks, consider PowerShell's native scheduling:

$trigger = New-JobTrigger -Once -At "6:50PM" -RepeatIndefinitely -RepetitionInterval "00:10:00"
Register-ScheduledJob -Name "10MinJob" -ScriptBlock {
    # Your code here
} -Trigger $trigger

When dealing with Windows Server 2008 SP2 Task Scheduler, I've encountered a scenario where a recurring task set to run every 10 minutes fails to trigger at the designated "Next Run Time." The scheduler UI updates the next execution time (e.g., from 8:00 PM to 8:10 PM) without actually executing the task, while manual execution works perfectly.

The problematic trigger shows this configuration in XML:

<Triggers>
    <CalendarTrigger>
        <StartBoundary>2012-06-18T18:50:00</StartBoundary>
        <Enabled>true</Enabled>
        <ScheduleByDay>
            <DaysInterval>1</DaysInterval>
        </ScheduleByDay>
        <Repetition>
            <Interval>PT10M</Interval>
            <Duration>P1D</Duration>
        </Repetition>
    </CalendarTrigger>
</Triggers>

Before proceeding with solutions, verify these critical points:

• Task History: Check the "History" tab in Task Scheduler for error codes (even when Last Run Result shows 0x0)
• Account Permissions: Ensure the RUN AS account has "Log on as a batch job" rights (gpedit.msc → Computer Configuration → Windows Settings → Security Settings → Local Policies → User Rights Assignment)
• Power Settings: Confirm "Allow tasks to be run on demand" is enabled in Task Scheduler options

Here's a PowerShell script that completely recreates the task with reinforced settings:

$action = New-ScheduledTaskAction -Execute "powershell.exe" -Argument "-NoProfile -File C:\scripts\your_script.ps1"
$trigger = New-ScheduledTaskTrigger -Daily -At "6:50 PM" -RepetitionInterval (New-TimeSpan -Minutes 10)
$settings = New-ScheduledTaskSettingsSet -AllowStartIfOnBatteries -DontStopIfGoingOnBatteries -StartWhenAvailable -DontStopOnIdleEnd
Register-ScheduledTask -TaskName "Critical10MinTask" -Action $action -Trigger $trigger -Settings $settings -User "NT AUTHORITY\SYSTEM" -RunLevel Highest

For GUI users, follow these exact steps:

1. Right-click the task → Disable
2. Right-click → Export and save as backup
3. Delete the original task
4. Create new task with identical parameters
5. Under Conditions tab:
   • UNCHECK "Start the task only if the computer is on AC power"
   • CHECK "Wake the computer to run this task"
6. Under Settings tab:
   • CHECK "Run task as soon as possible after a scheduled start is missed"
   • Set "If the task fails, restart every:" to 1 minute

Use this PowerShell snippet to monitor task execution:

$taskName = "YourTaskName"
$startTime = (Get-Date).AddMinutes(-15)
Get-WinEvent -LogName "Microsoft-Windows-TaskScheduler/Operational" | 
    Where-Object { $_.TimeCreated -ge $startTime -and $_.Message -like "*$taskName*" } | 
    Select-Object TimeCreated, Message | 
    Format-Table -AutoSize