diff --git a/server/filesystem/filesystem.go b/server/filesystem/filesystem.go
index cb70b44..0fd051b 100644
--- a/server/filesystem/filesystem.go
+++ b/server/filesystem/filesystem.go
@@ -159,7 +159,7 @@ func (fs *Filesystem) Writefile(p string, r io.Reader) error {
 	// Adjust the disk usage to account for the old size and the new size of the file.
 	fs.addDisk(sz - currentSize)
 
-	return fs.Chown(cleaned)
+	return fs.unsafeChown(cleaned)
 }
 
 // Creates a new directory (name) at a specified path (p) for the server.
@@ -217,7 +217,12 @@ func (fs *Filesystem) Chown(path string) error {
 	if err != nil {
 		return err
 	}
+	return fs.unsafeChown(cleaned)
+}
 
+// unsafeChown chowns the given path, without checking if the path is safe. This should only be used
+// when the path has already been checked.
+func (fs *Filesystem) unsafeChown(path string) error {
 	if fs.isTest {
 		return nil
 	}
@@ -226,19 +231,19 @@ func (fs *Filesystem) Chown(path string) error {
 	gid := config.Get().System.User.Gid
 
 	// Start by just chowning the initial path that we received.
-	if err := os.Chown(cleaned, uid, gid); err != nil {
+	if err := os.Chown(path, uid, gid); err != nil {
 		return errors.Wrap(err, "server/filesystem: chown: failed to chown path")
 	}
 
 	// If this is not a directory we can now return from the function, there is nothing
 	// left that we need to do.
-	if st, err := os.Stat(cleaned); err != nil || !st.IsDir() {
+	if st, err := os.Stat(path); err != nil || !st.IsDir() {
 		return nil
 	}
 
 	// If this was a directory, begin walking over its contents recursively and ensure that all
 	// of the subfiles and directories get their permissions updated as well.
-	err = godirwalk.Walk(cleaned, &godirwalk.Options{
+	err := godirwalk.Walk(path, &godirwalk.Options{
 		Unsorted: true,
 		Callback: func(p string, e *godirwalk.Dirent) error {
 			// Do not attempt to chown a symlink. Go's os.Chown function will affect the symlink
@@ -255,7 +260,6 @@ func (fs *Filesystem) Chown(path string) error {
 			return os.Chown(p, uid, gid)
 		},
 	})
-
 	return errors.Wrap(err, "server/filesystem: chown: failed to chown during walk function")
 }
 
diff --git a/server/filesystem/path.go b/server/filesystem/path.go
index 8a439c3..3952e5d 100644
--- a/server/filesystem/path.go
+++ b/server/filesystem/path.go
@@ -2,6 +2,7 @@ package filesystem
 
 import (
 	"context"
+	iofs "io/fs"
 	"os"
 	"path/filepath"
 	"strings"
@@ -33,8 +34,6 @@ func (fs *Filesystem) IsIgnored(paths ...string) error {
 // This logic is actually copied over from the SFTP server code. Ideally that eventually
 // either gets ported into this application, or is able to make use of this package.
 func (fs *Filesystem) SafePath(p string) (string, error) {
-	var nonExistentPathResolution string
-
 	// Start with a cleaned up path before checking the more complex bits.
 	r := fs.unsafeFilePath(p)
 
@@ -44,47 +43,24 @@ func (fs *Filesystem) SafePath(p string) (string, error) {
 	if err != nil && !os.IsNotExist(err) {
 		return "", errors.Wrap(err, "server/filesystem: failed to evaluate symlink")
 	} else if os.IsNotExist(err) {
-		// The requested directory doesn't exist, so at this point we need to iterate up the
-		// path chain until we hit a directory that _does_ exist and can be validated.
-		parts := strings.Split(filepath.Dir(r), "/")
-
-		var try string
-		// Range over all of the path parts and form directory pathings from the end
-		// moving up until we have a valid resolution or we run out of paths to try.
-		for k := range parts {
-			try = strings.Join(parts[:(len(parts)-k)], "/")
-
-			if !fs.unsafeIsInDataDirectory(try) {
-				break
-			}
-
-			t, err := filepath.EvalSymlinks(try)
-			if err == nil {
-				nonExistentPathResolution = t
-				break
-			}
+		// The target of one of the symlinks (EvalSymlinks is recursive) does not exist.
+		// So we get what target path does not exist and check if it's within the data
+		// directory. If it is, we return the original path, otherwise we return an error.
+		pErr, ok := err.(*iofs.PathError)
+		if !ok {
+			return "", errors.Wrap(err, "server/filesystem: failed to evaluate symlink")
 		}
-	}
-
-	// If the new path doesn't start with their root directory there is clearly an escape
-	// attempt going on, and we should NOT resolve this path for them.
-	if nonExistentPathResolution != "" {
-		if !fs.unsafeIsInDataDirectory(nonExistentPathResolution) {
-			return "", NewBadPathResolution(p, nonExistentPathResolution)
-		}
-
-		// If the nonExistentPathResolution variable is not empty then the initial path requested
-		// did not exist and we looped through the pathway until we found a match. At this point
-		// we've confirmed the first matched pathway exists in the root server directory, so we
-		// can go ahead and just return the path that was requested initially.
-		return r, nil
+		ep = pErr.Path
 	}
 
 	// If the requested directory from EvalSymlinks begins with the server root directory go
 	// ahead and return it. If not we'll return an error which will block any further action
 	// on the file.
 	if fs.unsafeIsInDataDirectory(ep) {
-		return ep, nil
+		// Returning the original path here instead of the resolved path ensures that
+		// whatever the user is trying to do will work as expected. If we returned the
+		// resolved path, the user would be unable to know that it is in fact a symlink.
+		return r, nil
 	}
 
 	return "", NewBadPathResolution(p, r)
diff --git a/server/filesystem/path_test.go b/server/filesystem/path_test.go
index ebdb71a..ecb9627 100644
--- a/server/filesystem/path_test.go
+++ b/server/filesystem/path_test.go
@@ -115,6 +115,14 @@ func TestFilesystem_Blocks_Symlinks(t *testing.T) {
 		panic(err)
 	}
 
+	if err := os.Symlink(filepath.Join(rfs.root, "malicious_does_not_exist.txt"), filepath.Join(rfs.root, "/server/symlinked_does_not_exist.txt")); err != nil {
+		panic(err)
+	}
+
+	if err := os.Symlink(filepath.Join(rfs.root, "/server/symlinked_does_not_exist.txt"), filepath.Join(rfs.root, "/server/symlinked_does_not_exist2.txt")); err != nil {
+		panic(err)
+	}
+
 	if err := os.Symlink(filepath.Join(rfs.root, "/malicious_dir"), filepath.Join(rfs.root, "/server/external_dir")); err != nil {
 		panic(err)
 	}
@@ -128,6 +136,22 @@ func TestFilesystem_Blocks_Symlinks(t *testing.T) {
 			g.Assert(IsErrorCode(err, ErrCodePathResolution)).IsTrue()
 		})
 
+		g.It("cannot write to a non-existent file symlinked outside the root", func() {
+			r := bytes.NewReader([]byte("testing what the fuck"))
+
+			err := fs.Writefile("symlinked_does_not_exist.txt", r)
+			g.Assert(err).IsNotNil()
+			g.Assert(IsErrorCode(err, ErrCodePathResolution)).IsTrue()
+		})
+
+		g.It("cannot write to chained symlinks with target that does not exist outside the root", func() {
+			r := bytes.NewReader([]byte("testing what the fuck"))
+
+			err := fs.Writefile("symlinked_does_not_exist2.txt", r)
+			g.Assert(err).IsNotNil()
+			g.Assert(IsErrorCode(err, ErrCodePathResolution)).IsTrue()
+		})
+
 		g.It("cannot write a file to a directory symlinked outside the root", func() {
 			r := bytes.NewReader([]byte("testing"))