OK. I was able to create the error using the command line. The following are the steps I took. I sure hope this is helpful. (In the steps below, I changed the name of my company in the URL to xxx.)
(1) Create a local TestLib directory with a single file libfile.h. (2) Import this to repo. C:\Dev\rhf>svn import TestLib http://svn1.xxx.com/svn/rhf/TestLib -m"Initial import" (3) Delete the local TestLib and then checkout a WC. C:\Dev\rhf> svn checkout http://svn1.xxx.com/svn/rhf/TestLib At this point we have TestLib in the repo and a checked out WC. (4) Now create another local directory, TestPrj, with a single file prjfile.txt and import this to the repository. C:\Dev\rhf>svn import TestPrj http://svn1.xxx.com/svn/rhf/TestPrj -m"Initial import" (5) Delete the local TestPrj directory and checkout a WC. C:\Dev\rhf> svn checkout http://svn1.xxx.com/svn/rhf/TestPrj (6) Make the file TestLib/libfile.h an external file in TestPrj. (The Subversion book was very confusing here and I finally found this syntax from a google search.) C:\Dev\rhf\TestPrj>svn propset svn:externals "http://svn1.xxx.com/svn/rhf/TestLib/libfile.h libfile.h" . property 'svn:externals' set on '.' (7) Commit the change and update. C:\Dev\rhf\TestPrj>svn update Fetching external item into 'libfile.h' E libfile.h Updated external to revision 3076. Updated to revision 3076. (8) Check the status. C:\Dev\rhf\TestPrj>svn status -v 3076 3076 rfletcher . 3076 3075 rfletcher prjfile.txt X 3076 3072 rfletcher libfile.h Everything looks fine at this point, here and in the repo browser. (9) Now go to the WC of TestLib, modify and commit libfile.h. C:\Dev\rhf\TestLib>svn commit -m"test change" Sending libfile.h Transmitting file data . Committed revision 3077. (11) Check the status of TestLib C:\Dev\rhf\TestLib>svn status -v 3071 3071 rfletcher . 3077 3077 rfletcher libfile.h (12) Return to TestPrj and attempt to Update. This gives an error. C:\Dev\rhf\TestPrj>svn update svn: In file 'C:\Users\kueng\nightlybuilds\latest\TortoiseSVN\ext\subversion\subversion\libsv n_wc\update_editor.c' line 4603: assertion failed (status == svn_wc__db_status_added) (13) Check the status of TestPrj - note the !. C:\Dev\rhf\TestPrj>svn status -v ! L 3077 3076 rfletcher . 3076 3075 rfletcher prjfile.txt X 3076 3072 rfletcher libfile.h By the way, if I do a complete new checkout of TestPrj, libfile.h is modified as expected. Bob