diff --git a/Cargo.lock b/Cargo.lock
index 2f245d2d..d575510e 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -552,6 +552,7 @@ dependencies = [
  "encode_unicode",
  "libc",
  "once_cell",
+ "unicode-width",
  "windows-sys 0.59.0",
 ]
 
@@ -693,6 +694,7 @@ dependencies = [
  "cot-cli",
  "cot_codegen",
  "darling 0.21.0",
+ "dialoguer",
  "glob",
  "heck",
  "hex",
@@ -966,6 +968,19 @@ version = "1.6.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "abd57806937c9cc163efc8ea3910e00a62e2aeb0b8119f1793a978088f8f6b04"
 
+[[package]]
+name = "dialoguer"
+version = "0.11.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "658bce805d770f407bc62102fca7c2c64ceef2fbcb2b8bd19d2765ce093980de"
+dependencies = [
+ "console",
+ "shell-words",
+ "tempfile",
+ "thiserror 1.0.69",
+ "zeroize",
+]
+
 [[package]]
 name = "difflib"
 version = "0.4.0"
@@ -2986,6 +3001,12 @@ dependencies = [
  "lazy_static",
 ]
 
+[[package]]
+name = "shell-words"
+version = "1.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "24188a676b6ae68c3b2cb3a01be17fbf7240ce009799bb56d5b1409051e78fde"
+
 [[package]]
 name = "shlex"
 version = "1.3.0"
@@ -3865,6 +3886,12 @@ version = "0.1.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "e70f2a8b45122e719eb623c01822704c4e0907e7e426a05927e1a1cfff5b75d0"
 
+[[package]]
+name = "unicode-width"
+version = "0.2.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "4a1a07cc7db3810833284e8d372ccdc6da29741639ecc70c9ec107df0fa6154c"
+
 [[package]]
 name = "unicode-xid"
 version = "0.2.6"
diff --git a/Cargo.toml b/Cargo.toml
index 0d55f2d9..7b34fea9 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -76,6 +76,7 @@ darling = "0.21"
 deadpool-redis = { version = "0.21", default-features = false }
 derive_builder = "0.20"
 derive_more = "2"
+dialoguer = "0.11.0"
 digest = "0.10"
 email_address = "0.2.9"
 fake = "4"
diff --git a/cot-cli/Cargo.toml b/cot-cli/Cargo.toml
index 56d60a36..9d9b718c 100644
--- a/cot-cli/Cargo.toml
+++ b/cot-cli/Cargo.toml
@@ -31,6 +31,7 @@ clap-verbosity-flag = { workspace = true, features = ["tracing"] }
 darling.workspace = true
 cot.workspace = true
 cot_codegen = { workspace = true, features = ["symbol-resolver"] }
+dialoguer.workspace = true
 glob.workspace = true
 heck.workspace = true
 hex.workspace = true
diff --git a/cot-cli/src/args.rs b/cot-cli/src/args.rs
index 9b09f4f6..0a703913 100644
--- a/cot-cli/src/args.rs
+++ b/cot-cli/src/args.rs
@@ -40,6 +40,9 @@ pub struct ProjectNewArgs {
     pub name: Option<String>,
     #[command(flatten)]
     pub source: CotSourceArgs,
+    /// Skip interactive prompts and use defaults
+    #[arg(short, long)]
+    pub yes: bool,
 }
 
 #[derive(Debug, Subcommand)]
diff --git a/cot-cli/src/handlers.rs b/cot-cli/src/handlers.rs
index 07071553..bf429f6c 100644
--- a/cot-cli/src/handlers.rs
+++ b/cot-cli/src/handlers.rs
@@ -2,16 +2,48 @@ use std::path::PathBuf;
 
 use anyhow::Context;
 use clap::CommandFactory;
+use dialoguer::Confirm;
 
 use crate::args::{
     Cli, CompletionsArgs, ManpagesArgs, MigrationListArgs, MigrationMakeArgs, ProjectNewArgs,
 };
 use crate::migration_generator::{MigrationGeneratorOptions, list_migrations, make_migrations};
 use crate::new_project::{CotSource, new_project};
+use crate::utils::{StatusType, print_status_msg};
 
 pub fn handle_new_project(
-    ProjectNewArgs { path, name, source }: ProjectNewArgs,
+    ProjectNewArgs {
+        path,
+        name,
+        source,
+        yes,
+    }: ProjectNewArgs,
 ) -> anyhow::Result<()> {
+    let path = path
+        .canonicalize()
+        .with_context(|| format!("unable to canonicalize path: {}", path.display()))?;
+
+    if path.exists() && path.join("Cargo.toml").exists() {
+        if !yes {
+            let confirmed = Confirm::new()
+                .with_prompt(format!(
+                    "Directory '{}' is not empty. Overwrite?",
+                    path.display()
+                ))
+                .default(false)
+                .interact()?;
+            if !confirmed {
+                print_status_msg(StatusType::Error, "Aborted: directory not empty");
+                std::process::exit(0);
+            }
+        } else {
+            print_status_msg(
+                StatusType::Warning,
+                &format!("Overwriting existing files in `{}`", path.display()),
+            );
+        }
+    }
+
     let project_name = match name {
         None => {
             let dir_name = path
@@ -29,6 +61,10 @@ pub fn handle_new_project(
     } else {
         CotSource::PublishedCrate
     };
+    print_status_msg(
+        StatusType::Creating,
+        &format!("Creating project '{}' in: {}", project_name, path.display()),
+    );
     new_project(&path, &project_name, &cot_source).with_context(|| "unable to create project")
 }
 
@@ -96,6 +132,7 @@ mod tests {
                 use_git: false,
                 cot_path: None,
             },
+            yes: false,
         };
 
         let result = handle_new_project(args);
diff --git a/cot-cli/src/new_project.rs b/cot-cli/src/new_project.rs
index 1241bc15..9cf75252 100644
--- a/cot-cli/src/new_project.rs
+++ b/cot-cli/src/new_project.rs
@@ -1,5 +1,6 @@
 use std::path::Path;
 
+use anyhow::Context;
 use heck::ToPascalCase;
 use rand::rngs::StdRng;
 use rand::{RngCore, SeedableRng};
@@ -60,8 +61,9 @@ pub fn new_project(
         &format!("Cot project `{project_name}`"),
     );
 
-    if path.exists() {
-        anyhow::bail!("destination `{}` already exists", path.display());
+    if !path.exists() {
+        std::fs::create_dir_all(path)
+            .with_context(|| format!("failed to create directory `{}`", path.display()))?;
     }
 
     let project_struct_name = format!("{}Project", project_name.to_pascal_case());
@@ -69,22 +71,28 @@ pub fn new_project(
     let cot_source = cot_source.as_cargo_toml_source();
     let dev_secret_key = generate_secret_key();
 
-    for (file_name, content) in PROJECT_FILES {
+    for (template_name, content) in PROJECT_FILES {
         // Cargo reads and parses all files that are named "Cargo.toml" in a repository,
         // so we need a different name so that it doesn't fail on build.
-        let file_name = file_name.replace(".template", "");
-
-        let file_path = path.join(file_name);
-        trace!("Writing file: {:?}", file_path);
+        let file_name = template_name.replace(".template", "");
+        let file_path = path.join(&file_name);
+
+        if file_path.exists() {
+            print_status_msg(
+                StatusType::Warning,
+                &format!("Overwriting `{}`", file_path.display()),
+            );
+        } else {
+            trace!("Writing file: {:?}", file_path);
+        }
 
-        std::fs::create_dir_all(
-            file_path
-                .parent()
-                .expect("joined path should always have a parent"),
-        )?;
+        if let Some(dir) = file_path.parent() {
+            std::fs::create_dir_all(dir)
+                .with_context(|| format!("failed to create directory `{}`", dir.display()))?;
+        }
 
         std::fs::write(
-            file_path,
+            &file_path,
             content
                 .replace("{{ project_name }}", project_name)
                 .replace("{{ project_struct_name }}", &project_struct_name)
diff --git a/cot-cli/tests/new_project.rs b/cot-cli/tests/new_project.rs
index 9d272491..266b5560 100644
--- a/cot-cli/tests/new_project.rs
+++ b/cot-cli/tests/new_project.rs
@@ -18,6 +18,7 @@ fn new_project_compile_test() {
         &project_path,
         "my_project",
         &CotSource::Path(&cot_workspace_path),
+        false,
     )
     .unwrap();