diff --git a/CHANGELOG.md b/CHANGELOG.md
index d3e51cf0..eeebc685 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -24,6 +24,9 @@
 - Added `FileDialog::show_left_panel` to show or hide the left panel  [#54](https://github.com/fluxxcode/egui-file-dialog/pull/54)
 - Added `FileDialog::show_places`, `FileDialog::show_devices` and `FileDialog::show_removable_devices` to show or hide individual section of the left panel [#57](https://github.com/fluxxcode/egui-file-dialog/pull/57)
 
+### 🐛 Bug Fixes
+- Fixed not every path being canonicalized [#76](https://github.com/fluxxcode/egui-file-dialog/pull/76)
+
 ### 🔧 Changes
 - Cleanup and restructure `FileDialog` UI methods [#56](https://github.com/fluxxcode/egui-file-dialog/pull/56)
 
diff --git a/src/data/disks.rs b/src/data/disks.rs
index aefc0138..4280b6b7 100644
--- a/src/data/disks.rs
+++ b/src/data/disks.rs
@@ -1,3 +1,4 @@
+use std::fs;
 use std::path::{Path, PathBuf};
 
 /// Wrapper above the sysinfo::Disk struct.
@@ -14,7 +15,7 @@ impl Disk {
     /// Create a new Disk object based on the data of a sysinfo::Disk.
     pub fn from_sysinfo_disk(disk: &sysinfo::Disk) -> Self {
         Self {
-            mount_point: disk.mount_point().to_path_buf(),
+            mount_point: Self::canonicalize(disk.mount_point()),
             display_name: gen_display_name(disk),
             is_removable: disk.is_removable(),
         }
@@ -33,6 +34,15 @@ impl Disk {
     pub fn is_removable(&self) -> bool {
         self.is_removable
     }
+
+    /// Canonicalizes the given path.
+    /// Returns the input path in case of an error.
+    fn canonicalize(path: &Path) -> PathBuf {
+        match fs::canonicalize(path) {
+            Ok(p) => p,
+            Err(_) => path.to_path_buf(),
+        }
+    }
 }
 
 /// Wrapper above the sysinfo::Disks struct
@@ -72,7 +82,7 @@ fn gen_display_name(disk: &sysinfo::Disk) -> String {
         .to_str()
         .unwrap_or_default()
         .to_string()
-        .replace("\\", "");
+        .replace('\\', "");
 
     // Try using the mount point as the display name if the specified name
     // from sysinfo::Disk is empty or contains invalid characters
diff --git a/src/file_dialog.rs b/src/file_dialog.rs
index 8defc831..f31ed02c 100644
--- a/src/file_dialog.rs
+++ b/src/file_dialog.rs
@@ -236,16 +236,6 @@ impl FileDialog {
     ) -> io::Result<()> {
         self.reset();
 
-        // Try to use the parent directory if the initial directory is a file.
-        // If the path then has no parent directory, the user will see an error that the path
-        // does not exist. However, using the user directories or disks, the user is still able
-        // to select an item or save a file.
-        if self.config.initial_directory.is_file() {
-            if let Some(parent) = self.config.initial_directory.parent() {
-                self.config.initial_directory = parent.to_path_buf();
-            }
-        }
-
         if mode == DialogMode::SelectFile {
             show_files = true;
         }
@@ -269,7 +259,7 @@ impl FileDialog {
             };
         }
 
-        self.load_directory(&self.config.initial_directory.clone())
+        self.load_directory(&self.gen_initial_directory(&self.config.initial_directory))
     }
 
     /// Shortcut function to open the file dialog to prompt the user to select a directory.
@@ -1413,6 +1403,22 @@ impl FileDialog {
         self.state = DialogState::Cancelled;
     }
 
+    /// This function generates the initial directory based on the configuration.
+    /// The function does the following things:
+    ///   - Canonicalize the path if enabled
+    ///   - Attempts to use the parent directory if the path is a file
+    fn gen_initial_directory(&self, path: &Path) -> PathBuf {
+        let mut path = fs::canonicalize(path).unwrap_or(path.to_path_buf());
+
+        if path.is_file() {
+            if let Some(parent) = path.parent() {
+                path = parent.to_path_buf();
+            }
+        }
+
+        path
+    }
+
     /// Gets the currently open directory.
     fn current_directory(&self) -> Option<&Path> {
         if let Some(x) = self.directory_stack.iter().nth_back(self.directory_offset) {
@@ -1546,18 +1552,10 @@ impl FileDialog {
     ///
     /// The function also sets the loaded directory as the selected item.
     fn load_directory(&mut self, path: &Path) -> io::Result<()> {
-        let full_path = match fs::canonicalize(path) {
-            Ok(path) => path,
-            Err(err) => {
-                self.directory_error = Some(err.to_string());
-                return Err(err);
-            }
-        };
-
         // Do not load the same directory again.
         // Use reload_directory if the content of the directory should be updated.
         if let Some(x) = self.current_directory() {
-            if x == full_path {
+            if x == path {
                 return Ok(());
             }
         }
@@ -1567,7 +1565,7 @@ impl FileDialog {
                 .drain(self.directory_stack.len() - self.directory_offset..);
         }
 
-        self.directory_stack.push(full_path);
+        self.directory_stack.push(path.to_path_buf());
         self.directory_offset = 0;
 
         self.load_directory_content(path)?;