There is an issue with installing SP2 for Exchange 2007 on SBS 2008, Microsoft has released a tool to get passed the errors - link. You need to download and extract Exchange 2007 SP2 - link, run the install tool. It will ask for the directory of SP2, and then you install SP2 normally.

Here are more details of the issue on MSExchange.org

We recently implemented a new SBS 2008 server for one of our clients.  A user was going to be working from home and wanted to utilize thier corporate office desktop to get some tasks done.  They were able to authenticate to the Remote Web Workplace webpage successfully,  but were unable to connect to their Windows 7 desktop computer.  Every time they attempted to do so, their account was rejected with an error message: “The logon attempt failed”

I discovered the problem was due to an incorrect setting within IIS.

Here’s what I did to correct the problem:
I went to IIS Manager → Sites → SBS Web Applications → Rpc → Authentication.  There I found only “Basic Authentication” was enabled.

Enabled “Windows Authentication” then ran an IIS reset. When IIS came back online, I was able to connect via TS Gateway to the server and at least one workstation. I connected and disconnected multiple times and it had no problems. The end user verified they were also able to authenticate without error, and gained remote control of their Windows 7 computer.

When running WSUS on a Small Business Server, the default location is the C:\ drive, when that drive gets full you need to move the content and the SQL database. Below are the steps to move the SQL database to another location.

1. Open command prompt and type: net stop “update services”

2. Next, at the command promt type: net stop w3svc (if it is SBS 2008 it will also stop the Terminal Services Gateway, remember to restart)

3. Open Microsoft SQL Express Management Studio (if you don’t have this, go to http://tinyurl.com/ynl9tv to download) and connect to the MICROSOFT##SSEE database, which is the WSUS database and the SharePoint databases in SBS 2008. You can’t just connect to the database normally, you need to type this in server name area:   \\.\pipe\MSSQL$MICROSOFT##SSEE\sql\query

 4. Detach the SUSDB database, move the SUSDB folder to the new location and attach the database again with Management Studio

5. Restart the services: “update services”, “w3svc”, and “Terminal Services Gateway”

While going through a vulnerability scan for PCI compliancy, the report noted that IIS 7 on a Small Business Server 2008 was still using SSL v2.0 instead of SSL 3.0 or TLS 1.0. To disable SSL v2.0:

1. Click Start, click Run, type regedt32 or type regedit, and then click OK.
2. In Registry Editor, locate the following registry key:HKey_Local_Machine\System\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Protocols\SSL 2.0\Server
3. On the Edit menu, click Add Value.
4. In the Data Type list, click DWORD.
5. In the Value Name box, type Enabled, and then click OK.Note If this value is present, double-click the value to edit its current value.
6. Type 00000000 in Binary Editor to set the value of the new key equal to “0″.
7. Click OK. Restart the computer.

IIS negotiates the encryption with the client browser. An attacker could use a tool that tells the server it has only sslv2 (which is weaker) available. If you disable sslv2 it only uses v3 or tls, as requested by browser. A browser only supporting sslv2 would fail.

 This applies to Windows Server 2003, and Windows Server 2008, and both versions of SBS.

http://support.microsoft.com/default.aspx?scid=kb;en-us;187498

You run into issues installing Exchange 2007 SP2 on SBS 2008 until you add the following key and DWORD to the registry.

To create the E12SP2READY registry value, follow these steps:

1. Click Start, click Run, type regedit in the Open box, and then click OK.
2. Locate and then click the following registry subkey:
   HKEY_LOCAL_MACHINE\Software\Microsoft\SmallBusinessServer\Exchange

   Note If the Exchange subkey does not exist, you must create it. To do this, follow these steps:

   1. Right-click SmallBusinessServer, point to New on the Edit menu, and then click Key.
   2. Type Exchange and then press ENTER.
3. After you select the Exchange subkey that is specified in step 2, point to New on the Edit menu, and then click DWORD Value.
4. Type E12SP2READY, and then press ENTER.
5. Right-click E12SP2READY, and then click Modify.
6. In the Value data box, type 1, and then click OK.
7. On the File menu, click Exit to exit Registry Editor.

Full article at Microsoft - http://support.microsoft.com/kb/973862

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There are additional steps to get Exchange 2007 SP2 installed on SBS 2008, below are the steps to complete from Microsoft Support

http://support.microsoft.com/default.aspx?scid=kb;EN-US;973862

After installing the latest version of Trend Micro Scanmail 8.0 on an SBS 2008 server, the Exchange Transport service kept stopping and reporting the following errors in the Application event log:

Event ID: 16023 Source: MSExchangeTransportMicrosoft Exchange couldn’t start transport agents. The Microsoft Exchange Transport service will be stopped. Exception details: Failed to create type ‘TrendMicro.SMEX.hookE12TransportAgent.hookE12RoutingAgentFactory’ from assembly ‘D:\Program Files\Trend Micro\Smex\hookE12TransportAgent.dll’ due to error ‘Invalid agent assembly path.’ …

Event ID: 1052 Source: MSExchange Extensibility

The creation of an agent factory for the agent ‘ScanMail Routing Agent’ failed with error ‘Failed to create type ‘TrendMicro.SMEX.hookE12TransportAgent.hookE12RoutingAgentFactory’ from assembly ‘D:\Program Files\Trend Micro\Smex\hookE12TransportAgent.dll’ due to error ‘Invalid agent assembly path.’.’. Verify that the corresponding transport agent assembly and dependencies with the correct version are installed.

The issues turned out to be a permission issue on the SMEX program file directory.  Exchange uses the Network Service account for the Transport Service credentials but this account didnt get security permissions to the Trend Micro SMEX program folder after install.  Adding the appropriate read permissions did the trick.