diff --git a/src/filesystem/canonicalization.rs b/src/filesystem/canonicalization.rs
index 90843b7..6b4aa7d 100644
--- a/src/filesystem/canonicalization.rs
+++ b/src/filesystem/canonicalization.rs
@@ -5,6 +5,8 @@ use crate::filesystem::binding::Side;
 use crate::filesystem::substitution::Substitutor;
 use crate::filesystem::FileSystem;
 
+use super::ext::{PathBufExt, PathExt};
+
 pub trait Canonicalizer {
     fn canonicalize<P: AsRef<Path>>(&self, path: P, deref_final: bool) -> Result<PathBuf>;
 }
@@ -59,6 +61,8 @@ impl Canonicalizer for FileSystem {
             ));
         }
 
+        let trailing_slash = guest_path.with_trailing_slash();
+
         // build guest_path_new from user_path
         let mut guest_path_new = PathBuf::new();
 
@@ -133,13 +137,22 @@ impl Canonicalizer for FileSystem {
                         if let Some(comp) = next_comp {
                             new_user_path.push(comp);
                         }
-                        new_user_path.push(it);
+                        it.for_each(|comp| new_user_path.push(comp));
+                        if trailing_slash {
+                            // recover the trailing slash
+                            new_user_path.try_add_trailing_slash();
+                        }
                         // use new_user_path to call this function again and return
                         // TODO: Can be optimized by replacing `it`
                         return self.canonicalize(&new_user_path, deref_final);
                     }
                     // we cannot go through a path which is neither a directory nor a symlink
-                    if !is_last_component {
+                    if !is_last_component
+                        || (is_last_component
+                            && !file_type.is_dir()
+                            && !file_type.is_symlink()
+                            && trailing_slash)
+                    {
                         return Err(Error::errno_with_msg(
                             Errno::ENOTDIR,
                             "when canonicalizing an intermediate path",
diff --git a/tests/applets.bats b/tests/applets.bats
index ff3db04..0e82303 100644
--- a/tests/applets.bats
+++ b/tests/applets.bats
@@ -394,3 +394,30 @@ function script_test_should_not_follow {
     [ "$status" -eq 0 ]
 
 }
+
+
+
+function script_test_trailing_slash_in_symlink {
+    PATH=/bin
+
+    cd /tmp/test_trailing_slash_in_symlink
+
+    echo "hello world" > file
+    ln -s file link1
+    ln -s file/ link2
+    ln -s file/. link3
+
+    [[ "$(stat -L -c "%F" link1 2>&1)" == *"regular file"* ]]
+    [[ "$(stat -L -c "%F" link2 2>&1)" == *"Not a directory"* ]]
+    [[ "$(stat -L -c "%F" link3 2>&1)" == *"Not a directory"* ]]
+
+}
+
+@test "test trailing slash in symlink" {
+    local test_dir="$ROOTFS/tmp/test_trailing_slash_in_symlink"
+    mkdir "$test_dir"
+    runp proot-rs --rootfs "$ROOTFS" -- /bin/sh -e -x -c "$(declare -f script_test_trailing_slash_in_symlink); script_test_trailing_slash_in_symlink"
+    rm -rf "$test_dir"
+    [ "$status" -eq 0 ]
+
+}