Case statement nested in WITH Statement not selecting a case - vba

Question

I am trying to set cell "H2" to either "Shift 1" , "Shift 2" or "Shift 3" depending on the inputted time value found in Cell D2 of my workbook, here is a screenshot example:
So Cell H2 is Shift 1 because it's within a Timevalue of Case TimeValue("11:21 PM") To TimeValue("7:20 AM")
Here is the code, it executes but doesn't select a case and I can't figure out my mistake. Also, if there is anyway to execute these 3 case statements within the With statement as I set the time input in cell "D2" inside of that with statement I would appreciate that!
.Range("D2").Value = Now 'Inputs the Time Value as the current Time
.Range("D2").NumberFormat = "h:mm:ss AM/PM" 'Formats the Time value as a Time entry
The code can be found below:
Sub ReportGeneratorTest()
Application.ScreenUpdating = False 'This speeds up the macro by hiding what the macro is doing
Application.EnableEvents = False
Application.Calculation = xlCalculationManual
Set wb3 = Workbooks.Open(Filename:="\\Report Generator\SetupSheet Report Generator.xlsm") 'Sets the Workbook variable as the database filepath
With wb3.Sheets("All Requests Sheet 1") 'With the "Changes" sheet do the following
.Rows("2:2").Insert Shift:=xlDown, CopyOrigin:=xlFormatFromRightOrBelow 'Inserts a new row in [3] with the same format as below
.Range("A2").Value = Sheet1.Range("K112").Value 'Inputs the typed in Operator name into the Report Generator
.Range("B2").Value = Sheet1.Range("H4").Value 'Inputs the "Key" inside cell "A" of the new row
.Range("C2").Value = Now 'Inputs the Date Submitted value as the current date
.Range("C2").NumberFormat = "dd-mmm-yyyy" 'Formats the Date Submitted value as a date entry
.Range("D2").Value = Now 'Inputs the Time Value as the current Time
.Range("D2").NumberFormat = "h:mm:ss AM/PM" 'Formats the Time value as a Time entry
.Range("E2").Value = UCase(Sheet1.Range("E4").Value) 'Inputs the Part inside Cell "D" of the new row
.Range("F2").Value = Sheet1.Range("E5").Value 'Inputs the Process inside Cell "E" of the new row
.Range("G2").Value = "IRR 200-2S"
End With
Dim T1 As Date
'T1 = Range("D2").Value
T1 = Now
'Set T1 = Range("D2").Value
Select Case T1
Case TimeValue("7:21 AM") To TimeValue("3:20 PM")
Range("H2").Value = "Shift 2"
Case TimeValue("3:21 PM") To TimeValue("11:20 PM")
Range("H2").Value = "Shift 3"
Case Else 'If the Timevalue is between TimeValue("11:21 PM") To TimeValue("7:20 AM")
Range("H2").Value = "Shift 1"
End Select
wb3.Save 'Save the database Workbook
wb3.Close False
Application.Calculation = xlCalculationAutomatic
Application.EnableEvents = True
Application.ScreenUpdating = True 'Must be "True" after running the code to be able to Read/Write the Workbook
End Sub

Answer 1

Summarizing the comments into an answer:
Case TimeValue("11:21 PM") To TimeValue("7:20 AM") doesn't work because when using To, the smaller value should come first. Maybe just move the "Shift 1" logic to a Case Else.
More importantly, Now includes today's date, i.e. it has both a day and time component. To get only the time component, you could do the following:
Dim T1 As Double
T1 = Now - Date