diff --git a/commands/hugo.go b/commands/hugo.go
index eaf75e329..9b827bc9b 100644
--- a/commands/hugo.go
+++ b/commands/hugo.go
@@ -829,6 +829,11 @@ func (c *commandeer) newWatcher(port int) error {
 							if err := watcher.Add(path); err != nil {
 								return err
 							}
+						} else if !c.isStatic(path) {
+							// Hugo's rebuilding logic is entirely file based. When you drop a new folder into
+							// /content on OSX, the above logic will handle future watching of those files,
+							// but the initial CREATE is lost.
+							dynamicEvents = append(dynamicEvents, fsnotify.Event{Name: path, Op: fsnotify.Create})
 						}
 						return nil
 					}
@@ -841,9 +846,7 @@ func (c *commandeer) newWatcher(port int) error {
 						}
 					}
 
-					isstatic := strings.HasPrefix(ev.Name, c.PathSpec().GetStaticDirPath()) || (len(c.PathSpec().GetThemesDirPath()) > 0 && strings.HasPrefix(ev.Name, c.PathSpec().GetThemesDirPath()))
-
-					if isstatic {
+					if c.isStatic(ev.Name) {
 						staticEvents = append(staticEvents, ev)
 					} else {
 						dynamicEvents = append(dynamicEvents, ev)
@@ -999,6 +1002,10 @@ func (c *commandeer) newWatcher(port int) error {
 	return nil
 }
 
+func (c *commandeer) isStatic(path string) bool {
+	return strings.HasPrefix(path, c.PathSpec().GetStaticDirPath()) || (len(c.PathSpec().GetThemesDirPath()) > 0 && strings.HasPrefix(path, c.PathSpec().GetThemesDirPath()))
+}
+
 // isThemeVsHugoVersionMismatch returns whether the current Hugo version is
 // less than the theme's min_version.
 func (c *commandeer) isThemeVsHugoVersionMismatch() (mismatch bool, requiredMinVersion string) {
diff --git a/hugolib/page.go b/hugolib/page.go
index cb9a28f24..42ed4e60f 100644
--- a/hugolib/page.go
+++ b/hugolib/page.go
@@ -322,6 +322,18 @@ func (ps Pages) FindPagePosByFilePath(inPath string) int {
 	return -1
 }
 
+func (ps Pages) FindPagePosByFilePathPrefix(prefix string) int {
+	if prefix == "" {
+		return -1
+	}
+	for i, x := range ps {
+		if strings.HasPrefix(x.Source.Path(), prefix) {
+			return i
+		}
+	}
+	return -1
+}
+
 // FindPagePos Given a page, it will find the position in Pages
 // will return -1 if not found
 func (ps Pages) FindPagePos(page *Page) int {
diff --git a/hugolib/page_collections.go b/hugolib/page_collections.go
index 4360f9315..b31738846 100644
--- a/hugolib/page_collections.go
+++ b/hugolib/page_collections.go
@@ -137,6 +137,18 @@ func (c *PageCollections) addPage(page *Page) {
 	c.rawAllPages = append(c.rawAllPages, page)
 }
 
+// When we get a REMOVE event we're not always getting all the individual files,
+// so we need to remove all below a given path.
+func (c *PageCollections) removePageByPathPrefix(path string) {
+	for {
+		i := c.rawAllPages.FindPagePosByFilePathPrefix(path)
+		if i == -1 {
+			break
+		}
+		c.rawAllPages = append(c.rawAllPages[:i], c.rawAllPages[i+1:]...)
+	}
+}
+
 func (c *PageCollections) removePageByPath(path string) {
 	if i := c.rawAllPages.FindPagePosByFilePath(path); i >= 0 {
 		c.rawAllPages = append(c.rawAllPages[:i], c.rawAllPages[i+1:]...)
diff --git a/hugolib/site.go b/hugolib/site.go
index 929dd590f..a172edd6a 100644
--- a/hugolib/site.go
+++ b/hugolib/site.go
@@ -667,11 +667,11 @@ func (s *Site) reProcess(events []fsnotify.Event) (whatChanged, error) {
 		seen[ev] = true
 
 		if s.isContentDirEvent(ev) {
-			logger.Println("Source changed", ev.Name)
+			logger.Println("Source changed", ev)
 			sourceChanged = append(sourceChanged, ev)
 		}
 		if s.isLayoutDirEvent(ev) {
-			logger.Println("Template changed", ev.Name)
+			logger.Println("Template changed", ev)
 			tmplChanged = append(tmplChanged, ev)
 
 			if strings.Contains(ev.Name, "shortcodes") {
@@ -682,11 +682,11 @@ func (s *Site) reProcess(events []fsnotify.Event) (whatChanged, error) {
 			}
 		}
 		if s.isDataDirEvent(ev) {
-			logger.Println("Data changed", ev.Name)
+			logger.Println("Data changed", ev)
 			dataChanged = append(dataChanged, ev)
 		}
 		if s.isI18nEvent(ev) {
-			logger.Println("i18n changed", ev.Name)
+			logger.Println("i18n changed", ev)
 			i18nChanged = append(dataChanged, ev)
 		}
 	}
@@ -761,7 +761,7 @@ func (s *Site) reProcess(events []fsnotify.Event) (whatChanged, error) {
 		if ev.Op&fsnotify.Remove == fsnotify.Remove {
 			//remove the file & a create will follow
 			path, _ := helpers.GetRelativePath(ev.Name, s.getContentDir(ev.Name))
-			s.removePageByPath(path)
+			s.removePageByPathPrefix(path)
 			continue
 		}