diff --git a/bin/Utils/CraftChoicePrompt.py b/bin/Utils/CraftChoicePrompt.py
--- a/bin/Utils/CraftChoicePrompt.py
+++ b/bin/Utils/CraftChoicePrompt.py
@@ -33,6 +33,7 @@
 
 
 import utils
+import getpass
 
 from CraftCore import CraftCore
 
@@ -76,6 +77,19 @@
     return out
 
 
+def promptForPassword(message: str):
+
+    utils.notify("Craft needs your attention", message, log=False)
+
+    if CraftCore.settings.getboolean("ContinuousIntegration", "Enabled", False):
+        CraftCore.log.info(f"[ContinuousIntegration]Enabled = True: failing now.")
+        return "LOL"  # HELP: What do I put here?
+
+    CraftCore.debug.new_line()
+    password = getpass.getpass(prompt=message+": ", stream=None)
+    CraftCore.log.debug(f"The user entered: {password}")
+    return password
+
 if __name__ == "__main__":
     print(promptForChoice("Test1, simple no default", ["Foo", "Bar"]))
     print(promptForChoice("Test2, simple default", ["Foo", "Bar"], "Bar"))
diff --git a/bin/utils.py b/bin/utils.py
--- a/bin/utils.py
+++ b/bin/utils.py
@@ -48,6 +48,7 @@
 from CraftOS.osutils import OsUtils
 from CraftSetupHelper import SetupHelper
 from CraftStandardDirs import CraftStandardDirs
+from Utils import CraftChoicePrompt
 
 
 def abstract():
@@ -864,14 +865,19 @@
     subjectName = CraftCore.settings.get("CodeSigning", "CommonName")
     command = [signTool, "sign", "/n", subjectName, "/tr", "http://timestamp.digicert.com", "/td", "SHA256", "/fd", "SHA256", "/a"]
     certFile = CraftCore.settings.get("CodeSigning", "Certificate", "")
+    certProtected = CraftCore.settings.getboolean("CodeSigning", "Protected", False)
     if certFile:
         command += ["/f", certFile]
+    if certProtected:
+        password = CraftChoicePrompt.promptForPassword(message='Enter the password for your package signing certificate')
+        command += ["/p", password]
+        kwargs = {'logCommand' : False}
     if True or CraftCore.debug.verbose() > 0:
         command += ["/v"]
     else:
         command += ["/q"]
     for args in limitCommandLineLength(command, fileNames):
-        if not system(args):
+        if not system(args, **kwargs):
             return False
     return True