Have you came across the scenario where you are performing a version upgrade of SQL Server as per supported path described here but still you are facing below error message during rules check?

<Error>
Error:
========
Rule "SQL Server 2008 R2 Feature" failed.

The specified edition upgrade is not supported. For information about  supported upgrade paths, see the SQL Server 2008 R2 version  and edition upgrade matrix in books online.
</Error>

If you look at Detail.txt file created by setup, search for “FeatureUpgradeMatrixCheck” and have a closer look at the log. From the highlighted you can easily understand the source and destination version+edition. So as per below log, setup is trying to upgrade from SQL 2000 Standard to Evaluation Edition (which is not in the link I provided earlier)

2011-01-27 22:53:34 Slp: Init rule target object: Microsoft.SqlServer.Configuration.SetupExtension.SkuUpgradeRule
2011-01-27 22:53:34 Slp: — SkuUpgradeRule : Rule ‘FeatureUpgradeMatrixCheck’ looking for previous version upgrade data for feature package ‘sql_as_Cpu32’.
2011-01-27 22:53:34 Slp: — SkuUpgradeRule : Rule ‘FeatureUpgradeMatrixCheck’ feature package ‘sql_as_Cpu32’ found no upgrade features.
2011-01-27 22:53:34 Slp: — SkuUpgradeRule : Rule ‘FeatureUpgradeMatrixCheck’ looking for previous version upgrade data for feature package ‘sql_engine_core_inst_Cpu32’.
2011-01-27 22:53:34 Slp: — SkuUpgradeRule : Found feature package  ‘Sql2000Ent_Cpu32’ with SkuValue=STANDARD ProductVersion=8.00.2039
2011-01-27 22:53:34 Slp: — SkuUpgradeRule : Rule ‘FeatureUpgradeMatrixCheck’ found sourceVersion 8.0 and edition STANDARD for feature package ‘sql_engine_core_inst_Cpu32’.
2011-01-27 22:53:34 Slp: — SkuPublicConfigObject : ValidateSkuMatrix checking sku matrix for sourceVersion=8.0 sourceEdition=STANDARD sourceArchitecture=X86 targetEdition=EVAL targetArchitecture=X86
2011-01-27 22:53:34 Slp: — SkuPublicConfigObject : ValidateSkuMatrix source and target architecture match.
2011-01-27 22:53:34 Slp: — SkuPublicConfigObject : ValidateSkuMatrix did not find a match in sku matrix .
2011-01-27 22:53:34 Slp: — SkuUpgradeRule : Rule ‘FeatureUpgradeMatrixCheck’ feature package ‘sql_engine_core_inst_Cpu32’ is blocking upgrade.
2011-01-27 22:53:34 Slp: — SkuUpgradeRule : Rule ‘FeatureUpgradeMatrixCheck’ detection result: IsValidFeatureUpgrade=False
2011-01-27 22:53:34 Slp: Evaluating rule        : FeatureUpgradeMatrixCheck
2011-01-27 22:53:34 Slp: Rule running on machine: SQLSERVER
2011-01-27 22:53:34 Slp: Rule evaluation done   : Failed
2011-01-27 22:53:34 Slp: Rule evaluation message: The specified edition upgrade is not supported. For information about supported upgrade paths, see the SQL Server 2008 R2 version and edition upgrade matrix in Books Online.
2011-01-27 22:53:34 Slp: Send result to channel : RulesEngineNotificationChannel
2011-01-27 22:53:34 Slp: Initializing rule      : Incomplete upgrade
2011-01-27 22:53:34 Slp: Rule applied features  : SQL;SQLEng

On a side note, Do you know the media difference for Standard and Evaluation edition? Well, there is no difference! Its the PID (Product ID) in below screen which decides the edition to be installed. The value of PID is picked from DefaultSetup.Ini file located on media. If there is no such file on Media then it would be enterprise evaluation edition of SQL Server.

Here is the little test which would prove the theory. I swear to god that I have not hit cancel while doing the test. Its the same media used for all the screen (Evaluation Media) All I did was change value in Enter the Product Key and hit next> or previous<.

Since I had media for various editions (How? Did I tell you that I work with Microsoft SQL Support team.. lol!), I copied/pasted the PID from DefaultSetup.ini file and rest can be seen above.

You might say, Nice to know what’s happening behind the scene but what you need to do if you run into such situation. In my scenario customer informed that they purchased Standard edition of SQL Server 2008 R2 still its taking EVAL in targetEdition and there has to be flaw somewhere. Later we found that screen was selecting Enterprise Evaluation by default (not sure why) So once he entered the Product Key, it worked like a charm!

Now, go ahead with the setup and post a comment here if this helped.

Cheers,
Balmukund Lakhani
Twitter @blakhani