diff --git a/crates/nu-cli/src/lib.rs b/crates/nu-cli/src/lib.rs
index 11d5c3ea7f..9c4cf2d1bb 100644
--- a/crates/nu-cli/src/lib.rs
+++ b/crates/nu-cli/src/lib.rs
@@ -17,6 +17,7 @@ mod evaluate;
 mod format;
 mod futures;
 mod git;
+mod path;
 mod shell;
 mod stream;
 mod utils;
diff --git a/crates/nu-cli/src/path.rs b/crates/nu-cli/src/path.rs
new file mode 100644
index 0000000000..ce384ae0ff
--- /dev/null
+++ b/crates/nu-cli/src/path.rs
@@ -0,0 +1,184 @@
+// Copyright (C) 2020 Kevin Dc
+//
+// This file is part of nushell.
+//
+// nushell is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// nushell is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with nushell.  If not, see <http://www.gnu.org/licenses/>.
+
+use std::io;
+use std::path::{Component, Path, PathBuf};
+
+pub fn normalize(path: impl AsRef<Path>) -> PathBuf {
+    let mut normalized = PathBuf::new();
+    for component in path.as_ref().components() {
+        match component {
+            Component::Normal(normal) => {
+                if let Some(normal) = normal.to_str() {
+                    if normal.chars().all(|c| c == '.') {
+                        for _ in 0..(normal.len() - 1) {
+                            normalized.push("..");
+                        }
+                    } else {
+                        normalized.push(normal);
+                    }
+                } else {
+                    normalized.push(normal);
+                }
+            }
+            c => normalized.push(c.as_os_str()),
+        }
+    }
+
+    normalized
+}
+
+pub struct AllowMissing(pub bool);
+
+pub fn canonicalize<P, Q>(
+    relative_to: P,
+    path: Q,
+    allow_missing: AllowMissing,
+) -> io::Result<PathBuf>
+where
+    P: AsRef<Path>,
+    Q: AsRef<Path>,
+{
+    let path = normalize(path);
+    let (relative_to, path) = if path.is_absolute() {
+        let components: Vec<_> = path.components().collect();
+        let separator = components
+            .iter()
+            .enumerate()
+            .find(|(_, c)| c == &&Component::CurDir || c == &&Component::ParentDir);
+
+        if let Some((index, _)) = separator {
+            let (absolute, relative) = components.split_at(index);
+            let absolute: PathBuf = absolute.iter().collect();
+            let relative: PathBuf = relative.iter().collect();
+
+            (absolute, relative)
+        } else {
+            (relative_to.as_ref().to_path_buf(), path)
+        }
+    } else {
+        (relative_to.as_ref().to_path_buf(), path)
+    };
+
+    let path = if path.is_relative() {
+        let mut result = relative_to;
+        path.components().for_each(|component| match component {
+            Component::ParentDir => {
+                result.pop();
+            }
+            Component::Normal(normal) => result.push(normal),
+            _ => {}
+        });
+
+        result
+    } else {
+        path
+    };
+
+    let path = match std::fs::read_link(&path) {
+        Ok(resolved) => resolved,
+        Err(e) => {
+            // We are here if path doesn't exist or isn't a symlink
+            if allow_missing.0 || path.exists() {
+                // Return if we allow missing paths or if the path
+                // actually exists, but wasn't a symlink
+                path
+            } else {
+                return Err(e);
+            }
+        }
+    };
+
+    // De-UNC paths
+    Ok(dunce::simplified(&path).to_path_buf())
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use std::io;
+
+    #[test]
+    fn normalize_three_dots() {
+        assert_eq!(PathBuf::from("../.."), normalize("..."));
+    }
+
+    #[test]
+    fn normalize_three_dots_with_redundant_dot() {
+        assert_eq!(PathBuf::from("./../.."), normalize("./..."));
+    }
+
+    #[test]
+    fn canonicalize_two_dots_and_allow_missing() -> io::Result<()> {
+        let relative_to = Path::new("/foo/bar"); // does not exists
+        let path = Path::new("..");
+
+        assert_eq!(
+            PathBuf::from("/foo"),
+            canonicalize(relative_to, path, AllowMissing(true))?
+        );
+
+        Ok(())
+    }
+
+    #[test]
+    fn canonicalize_three_dots_and_allow_missing() -> io::Result<()> {
+        let relative_to = Path::new("/foo/bar/baz"); // missing path
+        let path = Path::new("...");
+
+        assert_eq!(
+            PathBuf::from("/foo"),
+            canonicalize(relative_to, path, AllowMissing(true))?
+        );
+
+        Ok(())
+    }
+
+    #[test]
+    fn canonicalize_three_dots_with_redundant_dot_and_allow_missing() -> io::Result<()> {
+        let relative_to = Path::new("/foo/bar/baz"); // missing path
+        let path = Path::new("./...");
+
+        assert_eq!(
+            PathBuf::from("/foo"),
+            canonicalize(relative_to, path, AllowMissing(true))?
+        );
+
+        Ok(())
+    }
+
+    #[test]
+    fn canonicalize_three_dots_and_disallow_missing() -> io::Result<()> {
+        let relative_to = Path::new("/foo/bar/"); // root is not missing
+        let path = Path::new("...");
+
+        assert_eq!(
+            PathBuf::from("/"),
+            canonicalize(relative_to, path, AllowMissing(false))?
+        );
+
+        Ok(())
+    }
+
+    #[test]
+    fn canonicalize_three_dots_and_disallow_missing_should_fail() {
+        let relative_to = Path::new("/foo/bar/baz"); // foo is missing
+        let path = Path::new("...");
+
+        assert!(canonicalize(relative_to, path, AllowMissing(false)).is_err());
+    }
+}
diff --git a/crates/nu-cli/src/shell/filesystem_shell.rs b/crates/nu-cli/src/shell/filesystem_shell.rs
index 33fa049e21..45a86c46fb 100644
--- a/crates/nu-cli/src/shell/filesystem_shell.rs
+++ b/crates/nu-cli/src/shell/filesystem_shell.rs
@@ -5,6 +5,7 @@ use crate::commands::mkdir::MkdirArgs;
 use crate::commands::mv::MoveArgs;
 use crate::commands::rm::RemoveArgs;
 use crate::data::dir_entry_dict;
+use crate::path::{canonicalize, normalize, AllowMissing};
 use crate::prelude::*;
 use crate::shell::completer::NuCompleter;
 use crate::shell::shell::Shell;
@@ -187,13 +188,14 @@ impl Shell for FilesystemShell {
                 if target == Path::new("-") {
                     PathBuf::from(&self.last_path)
                 } else {
-                    let path = canonicalize(self.path(), target).map_err(|_| {
-                        ShellError::labeled_error(
-                            "Cannot change to directory",
-                            "directory not found",
-                            &v.tag,
-                        )
-                    })?;
+                    let path =
+                        canonicalize(self.path(), target, AllowMissing(false)).map_err(|_| {
+                            ShellError::labeled_error(
+                                "Cannot change to directory",
+                                "directory not found",
+                                &v.tag,
+                            )
+                        })?;
 
                     if !path.is_dir() {
                         return Err(ShellError::labeled_error(
@@ -1164,48 +1166,3 @@ fn is_hidden_dir(dir: impl AsRef<Path>) -> bool {
         }
     }
 }
-
-fn normalize(path: impl AsRef<Path>) -> PathBuf {
-    let mut normalized = PathBuf::new();
-    for component in path.as_ref().components() {
-        match component {
-            Component::Normal(normal) => {
-                if let Some(normal) = normal.to_str() {
-                    if normal.chars().all(|c| c == '.') {
-                        for _ in 0..(normal.len() - 1) {
-                            normalized.push("..");
-                        }
-                    } else {
-                        normalized.push(normal);
-                    }
-                } else {
-                    normalized.push(normal);
-                }
-            }
-            c => normalized.push(c.as_os_str()),
-        }
-    }
-
-    normalized
-}
-
-fn canonicalize(relative_to: impl AsRef<Path>, path: impl AsRef<Path>) -> std::io::Result<PathBuf> {
-    let path = if path.as_ref().is_relative() {
-        let mut result = relative_to.as_ref().to_path_buf();
-        normalize(path.as_ref())
-            .components()
-            .for_each(|component| match component {
-                Component::ParentDir => {
-                    result.pop();
-                }
-                Component::Normal(normal) => result.push(normal),
-                _ => {}
-            });
-
-        result
-    } else {
-        path.as_ref().into()
-    };
-
-    dunce::canonicalize(path)
-}