How to make Outlook Calendar reminders stay on top in Windows 7

I had the same problem with Outlook 2010. Use the steps mentioned below, it works like a charm. Don't forget to enable all macros: Trust Center > Macro Settings.

• Create a Digital certificate for later: Hit Start and type 'certificate', select 'Digital Certificate for VBA Projects'
• Enter a name for your certificate. Click OK. Open Outlook and hit Alt + F11 to start the VBA editor.
• In the tree on the left, expand 'Microsoft Office Outlook Objects' and double click on 'ThisOutlookSession'

• Paste in this code:

  Private Declare PtrSafe Function FindWindowA Lib "user32" _
  (ByVal lpClassName As String, ByVal lpWindowName As String) As Long
  
  Private Declare PtrSafe Function SetWindowPos Lib "user32" ( _
  ByVal hwnd As Long, ByVal hWndInsertAfter As Long, _
  ByVal X As Long, ByVal Y As Long, ByVal cx As Long, _
  ByVal cy As Long, ByVal wFlags As Long) As Long
  
  Private Const SWP_NOSIZE = &H1
  Private Const SWP_NOMOVE = &H2
  Private Const FLAGS As Long = SWP_NOMOVE Or SWP_NOSIZE
  Private Const HWND_TOPMOST = -1
  
  Private Sub Application_Reminder(ByVal Item As Object)
  Dim ReminderWindowHWnd As Variant
  On Error Resume Next
  ReminderWindowHWnd = FindWindowA(vbNullString, "1 Reminder")
  SetWindowPos ReminderWindowHWnd, HWND_TOPMOST, 0, 0, 0, 0, FLAGS
  
  End Sub
  

• Sign the Macro so it will run: Tools > Digital Signature... and choose the certificate you created earlier

• Close the VBA window
• Enable all macros in File > Options > Trust Center > Trust Center Settings > Macro Settings

AutoHotKey can also be used to solve this. This script will put the reminder window on top without stealing focus (tested with Win10 / Outlook 2013)

TrayTip Script, Looking for Reminder window to put on top, , 16
SetTitleMatchMode  2 ; windows contains
loop {
  WinWait, Reminder(s), 
  WinSet, AlwaysOnTop, on, Reminder(s)
  WinRestore, Reminder(s)
  TrayTip Outlook Reminder, You have an outlook reminder open, , 16
  WinWaitClose, Reminder(s), ,30
}

AHK Script - Compiled EXE

The best answer I've found is here: How to get Outlook appointment reminders to pop up in front of other windows again using some simple VBA.

It entails adding a few lines of simple VBA code to "ThisOutlookSession". Now, it pops up a window every time. Much better.

• Create a Digital certificate for later
• Hit Start and type ‘certificate’, select ‘Digital Certificate for VBA Projects’
• Enter a name for your certificate
• Done
• Open Outlook and hit Alt + F11 to start the VBA editor.
• In the tree on the left, expand ‘Microsoft Office Outlook Objects' and double click on ‘ThisOutlookSession’

• Paste in this code, modifying the text in quotes to suit your preferences. Leave the quotes in.

  Private Sub Application_Reminder(ByVal Item As Object)
  
  
      If TypeOf Item Is AppointmentItem Then
      MsgBox "Message text", vbSystemModal, "Message title"
      End If
  
  
  End Sub
  

• Sign the Macro so it will run by going to Tools > Digital Signature… and choosing the certificate you created earlier

• Close the VBA window