diff --git a/src/cli/cmd/init/handlers/rust.rs b/src/cli/cmd/init/handlers/rust.rs
index 0878ef5e..0a0d14ae 100644
--- a/src/cli/cmd/init/handlers/rust.rs
+++ b/src/cli/cmd/init/handlers/rust.rs
@@ -2,9 +2,7 @@ use crate::cli::cmd::init::prompt::Prompt;
 
 use super::{Flake, Handler, Input, Project};
 
-const CARGO_TOOLS: &[&str] = &[
-    "audit", "bloat", "cross", "edit", "outdated", "udeps", "watch",
-];
+const CARGO_TOOLS: &[&str] = &["bloat", "edit", "outdated", "udeps", "watch"];
 
 pub(crate) struct Rust;
 
@@ -57,6 +55,18 @@ impl Handler for Rust {
                     .env_vars
                     .insert(String::from("RUST_BACKTRACE"), String::from("1"));
             }
+
+            if project.has_file("Cross.toml") && Prompt::bool("This project appears to use cross-rs. Would you like to add the cargo-cross tool to your environment?") {
+                flake.dev_shell_packages.push(String::from("cargo-cross"));
+            }
+
+            if project.has_file("deny.toml") && Prompt::bool("This project appears to use cargo-deny. Would you like to add it to your environment?") {
+                flake.dev_shell_packages.push(String::from("cargo-deny"));
+            }
+
+            if project.has_file("audit.toml") && Prompt::bool("This project appears to use cargo-audit. Would you like to add it to your environment?") {
+                flake.dev_shell_packages.push(String::from("cargo-audit"));
+            }
         }
     }
 }
diff --git a/src/cli/cmd/init/handlers/tools.rs b/src/cli/cmd/init/handlers/tools.rs
index d126f81b..10610819 100644
--- a/src/cli/cmd/init/handlers/tools.rs
+++ b/src/cli/cmd/init/handlers/tools.rs
@@ -16,10 +16,83 @@ impl Handler for Tools {
             flake.dev_shell_packages.push(attr);
         }
 
+        // Build tools
         if project.has_one_of(&["WORKSPACE", ".bazelrc", ".bazelversion", "BUILD.bazel"])
             && Prompt::for_tool("Bazel")
         {
             flake.dev_shell_packages.push(String::from("bazel"));
         }
+
+        // Deployment
+        if project.has_file("site.yml") && Prompt::for_tool("Ansible") {
+            flake.dev_shell_packages.push(String::from("ansible"));
+        }
+
+        if project.has_file("Pulumi.yaml") && Prompt::for_tool("Pulumi") {
+            flake.dev_shell_packages.push(String::from("pulumi"));
+        }
+
+        // SaaS deployment tools
+        if project.has_file("vercel.json") && Prompt::bool("This project appears to deploy to Vercel. Would you like to add the Vercel CLI to your environment?") {
+            flake.dev_shell_packages.push(String::from("nodePackages.vercel"));
+        }
+
+        if project.has_file("netlify.toml") && Prompt::bool("This project appears to deploy to Netlify. Would you like to add the Netlify CLI to your environment?") {
+            flake.dev_shell_packages.push(String::from("netlify-cli"));
+        }
+
+        if project.has_file("fly.toml") && Prompt::bool("This project appears to deploy to Fly. Would you like to add the Fly CLI to your environment?") {
+            flake.dev_shell_packages.push(String::from("flyctl"));
+        }
+
+        // Kubernetes tools
+        if project.has_file("Tiltfile") && Prompt::for_tool("Tilt") {
+            flake.dev_shell_packages.push(String::from("tilt"));
+        }
+
+        // Schema-driven development
+        if project.has_one_of(&["buf.yaml", "buf.lock", "buf.gen.yaml", "buf.work.yaml"])
+            && Prompt::for_tool("Buf")
+        {
+            flake.dev_shell_packages.push(String::from("buf"));
+        }
+
+        // Checkers
+        if project.has_file(".shellcheckrc") && Prompt::for_tool("ShellCheck") {
+            flake.dev_shell_packages.push(String::from("shellcheck"));
+        }
+
+        // Virtual machines
+        if project.has_file("Vagrantfile") && Prompt::for_tool("Vagrant") {
+            flake.dev_shell_packages.push(String::from("vagrant"));
+        }
+
+        // SQL tools
+        if project.has_file("sqlx-data.json") && Prompt::bool("This project appears to use sqlx for Rust. Would you like to add the sqlx CLI to your environment?") {
+            flake.dev_shell_packages.push(String::from("sqlx-cli"));
+        }
+
+        // Static site generation
+        if project.has_one_of(&["hugo.json", "hugo.toml", "hugo.yaml"]) && Prompt::for_tool("Hugo")
+        {
+            flake.dev_shell_packages.push(String::from("hugo"));
+        }
+
+        if project.has_one_of(&["_config.toml", "_config.toml"]) && Prompt::for_tool("Jekyll") {
+            flake
+                .dev_shell_packages
+                .push(String::from("rubyPackages.jekyll"));
+        }
+
+        if project.has_one_of(&["mkdocs.yaml", "mkdocs.yml"]) && Prompt::for_tool("MkDocs") {
+            flake.dev_shell_packages.push(String::from("mkdocs"));
+        }
+
+        // Git
+        if project.has_file(".pre-commit-config.yaml") && Prompt::for_tool("pre-commit-hooks") {
+            flake
+                .dev_shell_packages
+                .push(String::from("python311Packages.pre-commit-hooks"));
+        }
     }
 }