Looks like port is choking on the presence of README file?
white:~ root# port upgrade outdated
---> Fetching expat
---> Verifying checksum(s) for expat
---> Extracting expat
---> Configuring expat
---> Building expat with target all
---> Staging expat into destroot
---> Deactivating expat 2.0.0_1
---> Installing expat 2.0.0_2
---> Activating expat 2.0.0_2
---> Cleaning expat
---> Fetching freetype
---> Verifying checksum(s) for freetype
---> Extracting freetype
---> Applying patches to freetype
---> Configuring freetype
---> Building freetype with target all
---> Staging freetype into destroot
Error: Target com.apple.destroot returned: xinstall: Cannot stat: Readme, No such file or directory
Error: Unable to upgrade port: 1
---> Fetching file-roller
---> Verifying checksum(s) for file-roller
---> Extracting file-roller
---> Configuring file-roller
---> Building file-roller with target all
---> Staging file-roller into destroot
---> Deactivating file-roller 2.18.0_0
---> Installing file-roller 2.18.2_0
---> Activating file-roller 2.18.2_0
---> Cleaning file-roller
---> Staging freetype into destroot
Error: Target com.apple.destroot returned: xinstall: Cannot stat: Readme, No such file or directory
Error: Unable to upgrade port: 1
--
Paul Beard
Are you trying to win an argument or solve a problem?