diff --git a/src/workflow/ArcanistPatchWorkflow.php b/src/workflow/ArcanistPatchWorkflow.php
--- a/src/workflow/ArcanistPatchWorkflow.php
+++ b/src/workflow/ArcanistPatchWorkflow.php
@@ -463,7 +463,8 @@
     if ($repository_api instanceof ArcanistSubversionAPI) {
       $patch_err = 0;
 
-      $copies = array();
+      $file_copies = array();
+      $dir_copies = array();
       $deletes = array();
       $patches = array();
       $propset = array();
@@ -525,10 +526,15 @@
                 throw new ArcanistUserAbortException();
               }
             } else {
-              $copies[] = array(
+              $copy = array(
                 $change->getOldPath(),
                 $change->getCurrentPath(),
               );
+              if (is_dir($repository_api->getPath($copy[0]))) {
+                $dir_copies[] = $copy;
+              } else {
+                $file_copies[] = $copy;
+              }
             }
             break;
           case ArcanistDiffChangeType::TYPE_ADD:
@@ -549,9 +555,18 @@
         }
       }
 
-      // Before we start doing anything, create all the directories we're going
+      // TODO: The SVN patch workflow likely does not work on windows because
+      // of the (cd ...) stuff.
+
+
+      // Do directory copying first
+      foreach ($dir_copies as $copy) {
+        $this->executeSubversionCopy($repository_api, $copy);
+      }
+
+      // Create all the directories we're going
       // to add files to if they don't already exist.
-      foreach ($copies as $copy) {
+      foreach ($file_copies as $copy) {
         list($src, $dst) = $copy;
         $this->createParentDirectoryOf($dst);
       }
@@ -564,17 +579,8 @@
         $this->createParentDirectoryOf($add);
       }
 
-      // TODO: The SVN patch workflow likely does not work on windows because
-      // of the (cd ...) stuff.
-
-      foreach ($copies as $copy) {
-        list($src, $dst) = $copy;
-        passthru(
-          csprintf(
-            '(cd %s; svn cp %s %s)',
-            $repository_api->getPath(),
-            ArcanistSubversionAPI::escapeFileNameForSVN($src),
-            ArcanistSubversionAPI::escapeFileNameForSVN($dst)));
+      foreach ($file_copies as $copy) {
+        $this->executeSubversionCopy($repository_api, $copy);
       }
 
       foreach ($deletes as $delete) {
@@ -629,7 +635,7 @@
       foreach ($adds as $add) {
         passthru(
           csprintf(
-            '(cd %s; svn add %s)',
+            '(cd %s; svn add --force %s)',
             $repository_api->getPath(),
             ArcanistSubversionAPI::escapeFileNameForSVN($add)));
       }
@@ -835,6 +841,18 @@
     return 0;
   }
 
+  private function executeSubversionCopy(
+    ArcanistRepositoryAPI $repository_api,
+    array $copy) {
+    list($src, $dst) = $copy;
+    passthru(
+      csprintf(
+        '(cd %s; svn cp --parents %s %s)',
+        $repository_api->getPath(),
+        ArcanistSubversionAPI::escapeFileNameForSVN($src),
+        ArcanistSubversionAPI::escapeFileNameForSVN($dst)));
+  }
+
   private function getCommitMessage(ArcanistBundle $bundle) {
     $revision_id    = $bundle->getRevisionID();
     $commit_message = null;