diff --git a/src/builds.rs b/src/builds.rs
index 9addf1c..479e2a8 100644
--- a/src/builds.rs
+++ b/src/builds.rs
@@ -138,7 +138,7 @@ pub async fn handle_build_push(config_path: PathBuf, verbose: bool, message: Opt
     let config_dir = config_path
         .parent()
         .ok_or_else(|| anyhow::anyhow!("Config file has no parent directory"))?;
-    let upload_dir = config_dir.join(&wavedash_config.upload_dir);
+    let upload_dir = crate::util::clean_path(&config_dir.join(&wavedash_config.upload_dir));
 
     // Verify source directory exists
     if !upload_dir.exists() {
diff --git a/src/dev/mod.rs b/src/dev/mod.rs
index 47448d8..f68139a 100644
--- a/src/dev/mod.rs
+++ b/src/dev/mod.rs
@@ -23,6 +23,7 @@ use url::Url;
 use crate::auth::AuthManager;
 use crate::config::{self, EngineKind, WavedashConfig};
 use crate::file_staging::FileStaging;
+use crate::util::clean_path;
 
 mod cert;
 mod entrypoint;
@@ -106,7 +107,7 @@ pub async fn handle_dev(config_path: Option<PathBuf>, verbose: bool, no_open: bo
 
     let wavedash_config = WavedashConfig::load(&config_path)?;
     let config_dir = config_parent_dir(&config_path)?;
-    let upload_dir = config_dir.join(&wavedash_config.upload_dir);
+    let upload_dir = clean_path(&config_dir.join(&wavedash_config.upload_dir));
 
     if !upload_dir.exists() || !upload_dir.is_dir() {
         anyhow::bail!(
diff --git a/src/main.rs b/src/main.rs
index 7de2303..39d1082 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -5,6 +5,7 @@ mod dev;
 mod file_staging;
 mod init;
 mod updater;
+mod util;
 
 use anyhow::Result;
 use auth::{login_with_browser, AuthManager, AuthSource};
diff --git a/src/util.rs b/src/util.rs
new file mode 100644
index 0000000..264f1ee
--- /dev/null
+++ b/src/util.rs
@@ -0,0 +1,19 @@
+use std::path::{Component, Path, PathBuf};
+
+/// Collapse `.` segments so paths rendered in logs and errors don't end up
+/// with leading `./` noise when `wavedash.toml`'s `upload_dir` already starts
+/// with `./`. Display-only — does not touch the filesystem and does not
+/// resolve `..` (paths we consume come from `config_dir.join(upload_dir)`, so
+/// the `..` case is vanishingly rare and correctly passed through to the
+/// filesystem calls that follow).
+pub fn clean_path(p: &Path) -> PathBuf {
+    let cleaned: PathBuf = p
+        .components()
+        .filter(|c| !matches!(c, Component::CurDir))
+        .collect();
+    if cleaned.as_os_str().is_empty() {
+        PathBuf::from(".")
+    } else {
+        cleaned
+    }
+}