diff --git a/.github/workflows/windows10_build.yml b/.github/workflows/windows10_build.yml
index 20485f3f19e..efb9840adf6 100644
--- a/.github/workflows/windows10_build.yml
+++ b/.github/workflows/windows10_build.yml
@@ -17,7 +17,7 @@ concurrency:
 jobs:
   Windows-Build:
     name: Windows10 Build ENV
-    runs-on: windows-latest
+    runs-on: windows-2019
     # Configuring -------------
     steps:
       - name: Setup Windows Git Configuration # This is under the assumption that git is already installed on the system
diff --git a/build/nsis/setup.nsi b/build/nsis/setup.nsi
index 685e26bfc8e..901fab034b6 100644
--- a/build/nsis/setup.nsi
+++ b/build/nsis/setup.nsi
@@ -30,6 +30,7 @@
   !define MUI_HEADERIMAGE_BITMAP "assets\installer_horizontal.bmp"
   !define MUI_ABORTWARNING
   !define MUI_WELCOMEPAGE_TITLE "${SLUG} Setup"
+  !define UninstId "OpenBBTerminal" ; You might want to use a GUID here
 
 ;--------------------------------
 ; Pages
@@ -48,16 +49,144 @@
 
   ; Set UI language
   !insertmacro MUI_LANGUAGE "English"
+  
+  
+  Var /GLOBAL installerPath
 
+
+
+  
+  
+; StrContains
+; This function does a case sensitive searches for an occurrence of a substring in a string. 
+; It returns the substring if it is found. 
+; Otherwise it returns null(""). 
+; Written by kenglish_hi
+; Adapted from StrReplace written by dandaman32
+ 
+ 
+Var STR_HAYSTACK
+Var STR_NEEDLE
+Var STR_CONTAINS_VAR_1
+Var STR_CONTAINS_VAR_2
+Var STR_CONTAINS_VAR_3
+Var STR_CONTAINS_VAR_4
+Var STR_RETURN_VAR
+ 
+Function StrContains
+  Exch $STR_NEEDLE
+  Exch 1
+  Exch $STR_HAYSTACK
+  ; Uncomment to debug
+  ;MessageBox MB_OK 'STR_NEEDLE = $STR_NEEDLE STR_HAYSTACK = $STR_HAYSTACK '
+    StrCpy $STR_RETURN_VAR ""
+    StrCpy $STR_CONTAINS_VAR_1 -1
+    StrLen $STR_CONTAINS_VAR_2 $STR_NEEDLE
+    StrLen $STR_CONTAINS_VAR_4 $STR_HAYSTACK
+    loop:
+      IntOp $STR_CONTAINS_VAR_1 $STR_CONTAINS_VAR_1 + 1
+      StrCpy $STR_CONTAINS_VAR_3 $STR_HAYSTACK $STR_CONTAINS_VAR_2 $STR_CONTAINS_VAR_1
+      StrCmp $STR_CONTAINS_VAR_3 $STR_NEEDLE found
+      StrCmp $STR_CONTAINS_VAR_1 $STR_CONTAINS_VAR_4 done
+      Goto loop
+    found:
+      StrCpy $STR_RETURN_VAR $STR_NEEDLE
+      Goto done
+    done:
+   Pop $STR_NEEDLE ;Prevent "invalid opcode" errors and keep the
+   Exch $STR_RETURN_VAR  
+FunctionEnd
+ 
+!macro _StrContainsConstructor OUT NEEDLE HAYSTACK
+  Push `${HAYSTACK}`
+  Push `${NEEDLE}`
+  Call StrContains
+  Pop `${OUT}`
+!macroend
+ 
+!define StrContains '!insertmacro "_StrContainsConstructor"'
+  
+  
+;-------------------------------
+; Uninstall Previous Version if exists
+ 
+!macro UninstallExisting exitcode uninstcommand
+Push `${uninstcommand}`
+Call UninstallExisting
+Pop ${exitcode}
+!macroend
+Function UninstallExisting
+Exch $1 ; uninstcommand
+Push $2 ; Uninstaller
+Push $3 ; Len
+StrCpy $3 ""
+StrCpy $2 $1 1
+StrCmp $2 '"' qloop sloop
+sloop:
+	StrCpy $2 $1 1 $3
+	IntOp $3 $3 + 1
+	StrCmp $2 "" +2
+	StrCmp $2 ' ' 0 sloop
+	IntOp $3 $3 - 1
+	Goto run
+qloop:
+	StrCmp $3 "" 0 +2
+	StrCpy $1 $1 "" 1 ; Remove initial quote
+	IntOp $3 $3 + 1
+	StrCpy $2 $1 1 $3
+	StrCmp $2 "" +2
+	StrCmp $2 '"' 0 qloop
+run:
+	StrCpy $2 $1 $3 ; Path to uninstaller
+	StrCpy $1 161 ; ERROR_BAD_PATHNAME
+	GetFullPathName $3 "$2\.." ; $InstDir
+	IfFileExists "$2" 0 +4
+	ExecWait '"$2" /S _?=$3' $1 ; This assumes the existing uninstaller is a NSIS uninstaller, other uninstallers don't support /S nor _?=
+	IntCmp $1 0 "" +2 +2 ; Don't delete the installer if it was aborted
+	Delete "$2" ; Delete the uninstaller
+	RMDir "$3" ; Try to delete $InstDir
+	RMDir "$3\.." ; (Optional) Try to delete the parent of $InstDir
+Pop $3
+Pop $2
+Exch $1 ; exitcode
+FunctionEnd
+ 
+ 
+Function .onInit
+ReadRegStr $0 HKCU "Software\Software\Microsoft\Windows\CurrentVersion\Uninstall\${UninstId}" "UninstallString"
+${If} $0 != ""
+${AndIf} ${Cmd} `MessageBox MB_YESNO|MB_ICONQUESTION "It is highly recomended to uninstall the previous version of OpenBB Terminal - Please click Yes to proceed (Note - You will not lose your custom settings) - Or you can uninstall manually. " /SD IDYES IDYES`
+	!insertmacro UninstallExisting $0 $0
+	${If} $0 <> 0
+		MessageBox MB_YESNO|MB_ICONSTOP "Failed to uninstall, continue anyway?" /SD IDYES IDYES +2
+			Abort
+	${EndIf}
+${EndIf}
+FunctionEnd
+ 
 ;--------------------------------
 ; Section - Install App
 
   Section "-hidden app"
     SectionIn RO
-    SetOutPath "$INSTDIR"
+	${StrContains} $0 "\OpenBB" "$INSTDIR"
+	StrCmp $0 "" notfound
+	  MessageBox MB_OK 'Found string $0  $INSTDIR'
+	  SetOutPath "$INSTDIR"
+	  Goto done
+	notfound:
+		MessageBox MB_OK "$INSTDIR is 'bla'"
+		SetOutPath "$INSTDIR\OpenBB"
+		StrCpy $InstDir "$INSTDIR\OpenBB"
+		MessageBox MB_OK 'Did not find string   "$INSTDIR\OpenBB"  "$installerPath"'
+	done:
+
     File /r "app\*.*"
     WriteRegStr HKCU "Software\${NAME}" "" $INSTDIR
     WriteUninstaller "$INSTDIR\Uninstall.exe"
+	WriteRegStr HKCU "Software\Software\Microsoft\Windows\CurrentVersion\Uninstall\${UninstId}" "OpenBBTerminal" "OpenBB"
+	WriteRegStr HKCU "Software\Software\Microsoft\Windows\CurrentVersion\Uninstall\${UninstId}" "UninstallString" '"$InstDir\Uninstall.exe"'
+	WriteRegStr HKCU "Software\Software\Microsoft\Windows\CurrentVersion\Uninstall\${UninstId}" "QuietUninstallString" '"$InstDir\Uninstall.exe" /S'
   SectionEnd
 
 
@@ -102,15 +231,19 @@
 ; Section - Uninstaller
 
 Section "Uninstall"
-
+	
   ;Delete Shortcut
   Delete "$DESKTOP\${NAME}.lnk"
 
   ;Delete Directory
   Delete '$SMPROGRAMS\${Company}\${NAME}'
+  
+  ;Delete Reg Key
+  DeleteRegKey HKCU "Software\Software\Microsoft\Windows\CurrentVersion\Uninstall\${UninstId}"
 
   ;Delete Uninstall
   Delete "$INSTDIR\Uninstall.exe"
+  
 
   ;Delete Folder
   RMDir /r "$INSTDIR"
diff --git a/openbb_terminal/core/log/generation/settings_logger.py b/openbb_terminal/core/log/generation/settings_logger.py
index 394cf24e488..0da5f50025a 100644
--- a/openbb_terminal/core/log/generation/settings_logger.py
+++ b/openbb_terminal/core/log/generation/settings_logger.py
@@ -120,4 +120,8 @@ def do_rollover():
 
     for handler in logging.getLogger().handlers:
         if isinstance(handler, PathTrackingFileHandler):
-            handler.doRollover()
+            try:
+                handler.doRollover()
+            # Stop the PermissionError on Windows when the file is open
+            except PermissionError:
+                pass