Dynamic Web Templates will only update the content of pages that are attached it in the following circumstances:
Web pages attached to a DWT will always update if the page is open when the DWT is saved.
Closed web pages will only update if you have the option to allow hidden meta data files checked for the local website under Site | Site Settings, on the General tab as shown below:
Pages will not update if hidden meta data is not allowed. In addition when you move files from one location to another in your site only open pages will reflect the new location. On closed web pages the link will break.
Occasionally even if you have "Use meta data" checked the meta data will become corrupt. If unchecking the use meta data box, closing Expression Web. The reopening Expression Web and checking the box again still doesn't update all the pages using your DWT then try running Steve Easton's FP Cleaner for your version of Expression Web.
On Live Sites
If you are accessing via the FrontPage Server Extensions and are hosting on a Windows 2003 Web Server you will need to get the latest updates. Try this link http://support.microsoft.com/kb/911831 which should also work on Windows 2000 and XP but not on Vista or Linux.
You will not be able update pages attached to a DWT on a Linux server using the FPSE for Linux since they were out of mainstream support before the update to support DWTs working live on the server.
If you are using the ability in Expression Web to work live on the server using FTP you may have the ability to enable hidden meta files as you would working on your local computer but I have not tested it. If you do, please let me know how it works out. I suspect that due to security permission you will not be able to do so but I would be glad to have my suspicious proved to be groundless.