If condition being ignored - vb.net

Question

I'm currently writing code for a game called Caladont.
The game is about first player saying the word and the next one has to say the word that starts with last two letters of previous word.
The problem comes when I want to check if word contains less than 3 letters or if it's empty.
In the first cycle when list for filling is still empty, everything is fine.
However, after I type for example 5 or more words and type a single letter or leave it empty, it prints two "You've lost!" messages, which means that code from if statement is being ignored since it changes bool variable to false and is supposed to exit the While loop.
I've tried replacing ok = false with Exit While in condition which checks if words contains less than 3 letters and it worked, but I want to understand what is the problem.
The code can also be found here [Caladont game
GitHub](https://github.com/whistleblower91/VB.net/blob/master/Caladont%20game):
Module Module1
Sub Main()
Kaladont()
End Sub
Sub Kaladont()
Const msg As String = "You've lost!"
Dim list As New List(Of String)
Dim word As String
Dim i As Integer
Dim ok As Boolean
ok = True
While ok
Console.Write("Insert word:")
word = Console.ReadLine()
list.Add(word)
If word.Length < 3 Or word = "" Then
Console.WriteLine(msg)
ok = False
End If
If list.Count > 1 Then 'Skip checking first word
For i = 0 To list.Count - 2
If word.ToLower = lista(i).ToLower Then
Console.WriteLine(msg)
ok = False
End If
Next
If LastTwo(word) = "ka" Or LastTwo(word)="nt" Then
Console.WriteLine("KALADONT! You won!")
ok = False
End If
If FirstTwo(list.Last) <> LastTwo(list(list.Count - 2)) Then
Console.WriteLine(msg)
ok = False
End If
End If
End While
Check()
End Sub
Function FirstTwo(ByVal s1 As String) As String
Return Left(s1.ToLower, 2)
End Function
Function LastTwo(ByVal s2 As String) As String
Return Right(s2.ToLower, 2)
End Function
Sub Check()
Dim sign As Char
Console.WriteLine("Do you want to start new game? y\n")
sign = Console.ReadLine()
If sign = CChar("y") Then
Console.Clear()
Kaladont()
ElseIf sign = CChar("n") Then
Exit Sub
End If
End Sub
End Module
Any solutions?

Answer 1

Even if you set ok to false, it will still go inside the other loop, you'll need to use Else
If word.Length < 3 Or word = "" Then
Console.WriteLine(msg)
ok = False
Else If list.Count > 1 Then 'Skip checking first word
An other way would be to exit the while with End while.
If word.Length < 3 Or word = "" Then
Console.WriteLine(msg)
ok = False
Exit While
End If