diff --git a/src/cli/src/cmd/add.rs b/src/cli/src/cmd/add.rs
index dfb9ae081..ccc49ef55 100644
--- a/src/cli/src/cmd/add.rs
+++ b/src/cli/src/cmd/add.rs
@@ -48,7 +48,7 @@ impl RunCmd for AddCmd {
                     OxenError::basic_str(format!("Failed to get current directory: {}", e))
                 })?;
                 let joined_path = current_dir.join(p);
-                joined_path.canonicalize().or_else(|_| Ok(joined_path))
+                dunce::canonicalize(&joined_path).or_else(|_| Ok(joined_path))
             })
             .collect::<Result<Vec<PathBuf>, OxenError>>()?;
 
diff --git a/src/cli/src/cmd/rm.rs b/src/cli/src/cmd/rm.rs
index a68d8fa20..ff99fac29 100644
--- a/src/cli/src/cmd/rm.rs
+++ b/src/cli/src/cmd/rm.rs
@@ -52,7 +52,7 @@ impl RunCmd for RmCmd {
                     OxenError::basic_str(format!("Failed to get current directory: {}", e))
                 })?;
                 let joined_path = current_dir.join(p);
-                joined_path.canonicalize().or_else(|_| Ok(joined_path))
+                dunce::canonicalize(&joined_path).or_else(|_| Ok(joined_path))
             })
             .collect::<Result<Vec<PathBuf>, OxenError>>()?;
 
diff --git a/src/lib/src/core/v0_19_0/add.rs b/src/lib/src/core/v0_19_0/add.rs
index c1d3fd93b..20fbd19ad 100644
--- a/src/lib/src/core/v0_19_0/add.rs
+++ b/src/lib/src/core/v0_19_0/add.rs
@@ -190,7 +190,7 @@ pub fn process_add_dir(
     let path = path.clone();
     let repo = repo.clone();
     let maybe_head_commit = maybe_head_commit.clone();
-    let repo_path = repo.path.clone();
+    let repo_path = &repo.path.clone();
 
     use std::sync::atomic::{AtomicU64, Ordering};
     use std::sync::Arc;
@@ -314,7 +314,7 @@ fn add_file_inner(
     path: &Path,
     staged_db: &DBWithThreadMode<MultiThreaded>,
 ) -> Result<Option<StagedMerkleTreeNode>, OxenError> {
-    let repo_path = repo.path.clone();
+    let repo_path = &repo.path.clone();
     let versions_path = util::fs::oxen_hidden_dir(&repo.path)
         .join(VERSIONS_DIR)
         .join(FILES_DIR);
@@ -360,17 +360,31 @@ pub fn process_add_file(
     seen_dirs: &Arc<Mutex<HashSet<PathBuf>>>,
 ) -> Result<Option<StagedMerkleTreeNode>, OxenError> {
     log::debug!("process_add_file {:?}", path);
-    let relative_path = util::fs::path_relative_to_dir(path, repo_path)?;
-    let full_path = repo_path.join(&relative_path);
+    let mut relative_path = util::fs::path_relative_to_dir(path, repo_path)?;
+    let mut full_path = repo_path.join(&relative_path);
 
     if !full_path.is_file() {
-        // If it's not a file - no need to add it
-        // We handle directories by traversing the parents of files below
-        log::debug!("file is not a file - skipping add on {:?}", full_path);
-        return Ok(Some(StagedMerkleTreeNode {
-            status: StagedEntryStatus::Added,
-            node: MerkleTreeNode::default_dir(),
-        }));
+
+        // Fix for Windows CLI
+        // util::fs::path_relative_to_dir can fail if the capitalization of the input path differs from what it is in the working directory
+        // TODO: is there ever a situation where process_add_file will be called on a path that doesn't exist? That will be propogated as an error here
+        log::debug!("file {:?} was not found. Checking for Windows CLI path", full_path);
+        let canon_repo_path = dunce::canonicalize(repo_path)?;
+        let cli_path = util::fs::path_relative_to_dir(path, &canon_repo_path)?;
+        
+        if cli_path.is_file() {
+            relative_path = cli_path;
+            full_path = canon_repo_path.join(&relative_path);
+        } else {
+
+            // If it's not a file - no need to add it
+            // We handle directories by traversing the parents of files below
+            log::debug!("file is not a file - skipping add on {:?}", full_path);
+            return Ok(Some(StagedMerkleTreeNode {
+                status: StagedEntryStatus::Added,
+                node: MerkleTreeNode::default_dir(),
+            }));
+        }
     }
 
     // Check if the file is already in the head commit
diff --git a/src/lib/src/util/fs.rs b/src/lib/src/util/fs.rs
index e1c536382..a8375d6e0 100644
--- a/src/lib/src/util/fs.rs
+++ b/src/lib/src/util/fs.rs
@@ -1351,7 +1351,38 @@ pub fn path_relative_to_dir(
     let mut mut_path = path.to_path_buf();
     let mut components: Vec<PathBuf> = vec![];
     while mut_path.parent().is_some() {
-        // println!("Comparing {:?} => {:?} => {:?}", path, mut_path.parent(), dir);
+        log::debug!("Comparing {:?} => {:?} => {:?}", path, mut_path.parent(), dir);
+        if let Some(filename) = mut_path.file_name() {
+            if mut_path != dir {
+                components.push(PathBuf::from(filename));
+            } else {
+                break;
+            }
+        }
+
+        mut_path.pop();
+    }
+    components.reverse();
+
+    let mut result = PathBuf::new();
+    for component in components.iter() {
+        result = result.join(component);
+    }
+
+    Ok(result)
+}
+
+pub fn path_relative_to_canon_dir(
+    path: impl AsRef<Path>,
+    dir: impl AsRef<Path>,
+) -> Result<PathBuf, OxenError> {
+    let path = path.as_ref();
+    let dir = dunce::canonicalize(dir.as_ref())?;
+
+    let mut mut_path = path.to_path_buf();
+    let mut components: Vec<PathBuf> = vec![];
+    while mut_path.parent().is_some() {
+        log::debug!("Comparing {:?} => {:?} => {:?}", path, mut_path.parent(), dir);
         if let Some(filename) = mut_path.file_name() {
             if mut_path != dir {
                 components.push(PathBuf::from(filename));