I am developing two extensions. One of them when installed will properly ask the user ["Repair Install?"], and the other does not. I have verified that the Module Name, friendly name, and version, matches exactly in the DNN file. It refuses to prompt user to Repair Install, and therefore does not update the binaries. I have to manually FTP the binaries.

Hereis how identical the two are: 

• They both have a feature controller, and are not current implementing IUpgradeable.
• They both have 90% identical DNN files, one has a Settings/View/Edit aspx but that is the only difference
• They both have SQL Data Provider for the version, but the sql files currently do nothing (there for the future)

Please explain why that option is not popping up for my extension which is functionally and practically identical to the other extension. 

Alright I found out why this happens.... Guess I missed this somewhere in the documentation?? I certainly overlooked it when using a Diff tool to analyze the two DNN files mentioned in OP.

Visual Studio Version format (aka binary standard): Major.Minor.Build.Revision
1.1.0.0

DNN's Extension Version format (100% necessary): Major.Minor.Build
1.1.0

Suppose that's what happens when you try to get rid of Visual Studio warnings by adhering to standards that aren't always standard in practice. Though the Config->install->dependentAssembly matches the VStudio format, so I'm happy.

Was using the BuildScript to automatically update all references to version.
The Installed Extensions list gave it away. Problem solved! Thanks for the tips and guidance.