diff --git a/CHANGELOG.md b/CHANGELOG.md
index b9754b2b8..4cace8127 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,14 @@
 - [Rust](https://github.com/moonrepo/rust-plugin/blob/master/CHANGELOG.md)
 - [TOML schema](https://github.com/moonrepo/schema-plugin/blob/master/CHANGELOG.md)
 
+## Unreleased
+
+#### 🚀 Updates
+
+- WASM API
+  - Added a `ExecutableConfig.shim_env_vars` field.
+  - Updated `ExecutableConfig.shim_before_args` and `ExecutableConfig.shim_after_args` to support a list of strings.
+
 ## 0.25.0
 
 #### 🚀 Updates
diff --git a/Cargo.lock b/Cargo.lock
index cb6089a58..2bf5d17d5 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -2477,7 +2477,7 @@ dependencies = [
 
 [[package]]
 name = "proto_cli_shim"
-version = "0.0.1"
+version = "0.25.0"
 dependencies = [
  "ctrlc",
  "dirs 5.0.1",
@@ -2506,6 +2506,7 @@ dependencies = [
  "serde",
  "serde_json",
  "sha2",
+ "shell-words",
  "starbase_archive",
  "starbase_events",
  "starbase_sandbox",
diff --git a/Cargo.toml b/Cargo.toml
index c80e742f0..0e90c0cdd 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -22,6 +22,7 @@ semver = "1.0.20"
 serde = { version = "1.0.193", features = ["derive"] }
 serde_json = "1.0.108"
 sha2 = "0.10.8"
+shell-words = "1.1.0"
 starbase = "0.2.10"
 starbase_archive = { version = "0.2.5", features = [
 	"tar-gz",
diff --git a/crates/cli-shim/Cargo.toml b/crates/cli-shim/Cargo.toml
index 7398bd421..a2a7a6a99 100644
--- a/crates/cli-shim/Cargo.toml
+++ b/crates/cli-shim/Cargo.toml
@@ -1,6 +1,6 @@
 [package]
 name = "proto_cli_shim"
-version = "0.0.1"
+version = "0.25.0"
 edition = "2021"
 publish = false
 
@@ -16,3 +16,6 @@ serde_json = { workspace = true }
 shared_child = "1.0.0"
 sigpipe = "0.1.3"
 starbase = { workspace = true }
+
+[package.metadata.dist]
+dist = true
diff --git a/crates/cli-shim/src/main.rs b/crates/cli-shim/src/main.rs
index 87fa6c5c0..a16e8c090 100644
--- a/crates/cli-shim/src/main.rs
+++ b/crates/cli-shim/src/main.rs
@@ -9,12 +9,14 @@ use std::process::{Command, Stdio};
 use std::sync::Arc;
 use std::{env, fs, io, process};
 
+// Keep in sync with crates/core/src/shim_registry.rs
 #[derive(Default, Deserialize)]
 #[serde(default)]
 struct Shim {
     after_args: Vec<String>,
     alt_for: Option<String>,
     before_args: Vec<String>,
+    env_vars: HashMap<String, String>,
 }
 
 fn get_proto_home() -> Result<PathBuf> {
@@ -75,6 +77,8 @@ fn create_command(mut args: VecDeque<String>, shim_name: &str) -> Result<Command
         command.args(passthrough_args);
     }
 
+    command.envs(shim.env_vars);
+
     Ok(command)
 }
 
diff --git a/crates/cli/tests/install_uninstall_test.rs b/crates/cli/tests/install_uninstall_test.rs
index 2402a953d..ff1f3b958 100644
--- a/crates/cli/tests/install_uninstall_test.rs
+++ b/crates/cli/tests/install_uninstall_test.rs
@@ -134,6 +134,9 @@ mod install_uninstall {
         } else {
             assert!(sandbox.path().join(".proto/shims/node").exists());
         }
+
+        // Check that the registry was created also
+        assert!(sandbox.path().join(".proto/shims/registry.json").exists());
     }
 
     #[test]
diff --git a/crates/cli/tests/plugins_test.rs b/crates/cli/tests/plugins_test.rs
index b14223028..239704231 100644
--- a/crates/cli/tests/plugins_test.rs
+++ b/crates/cli/tests/plugins_test.rs
@@ -4,7 +4,9 @@ use futures::Future;
 use proto_core::{
     load_tool_from_locator, Id, PluginLocator, ProtoEnvironment, Tool, UnresolvedVersionSpec,
 };
+use starbase_sandbox::assert_snapshot;
 use std::env;
+use std::fs;
 use std::path::{Path, PathBuf};
 use utils::*;
 
@@ -127,6 +129,10 @@ mod plugins {
                 .arg("--version")
                 .assert()
                 .success();
+
+            assert_snapshot!(
+                fs::read_to_string(sandbox.path().join(".proto/shims/registry.json")).unwrap()
+            );
         }
 
         #[test]
@@ -143,6 +149,10 @@ mod plugins {
                 .arg("--version")
                 .assert()
                 .success();
+
+            assert_snapshot!(
+                fs::read_to_string(sandbox.path().join(".proto/shims/registry.json")).unwrap()
+            );
         }
 
         #[test]
@@ -159,6 +169,10 @@ mod plugins {
                 .arg("version")
                 .assert()
                 .success();
+
+            assert_snapshot!(
+                fs::read_to_string(sandbox.path().join(".proto/shims/registry.json")).unwrap()
+            );
         }
 
         #[test]
@@ -177,6 +191,10 @@ mod plugins {
                 .arg("--version")
                 .assert()
                 .success();
+
+            assert_snapshot!(
+                fs::read_to_string(sandbox.path().join(".proto/shims/registry.json")).unwrap()
+            );
         }
 
         #[test]
@@ -203,6 +221,10 @@ mod plugins {
                 .arg("--version")
                 .assert()
                 .success();
+
+            assert_snapshot!(
+                fs::read_to_string(sandbox.path().join(".proto/shims/registry.json")).unwrap()
+            );
         }
 
         #[test]
@@ -229,6 +251,10 @@ mod plugins {
                 .arg("--version")
                 .assert()
                 .success();
+
+            assert_snapshot!(
+                fs::read_to_string(sandbox.path().join(".proto/shims/registry.json")).unwrap()
+            );
         }
 
         #[test]
@@ -255,6 +281,10 @@ mod plugins {
                 .arg("--version")
                 .assert()
                 .success();
+
+            assert_snapshot!(
+                fs::read_to_string(sandbox.path().join(".proto/shims/registry.json")).unwrap()
+            );
         }
 
         #[test]
@@ -264,27 +294,31 @@ mod plugins {
             create_proto_command(sandbox.path())
                 .arg("install")
                 .arg("python")
+                .arg("3.12.0") // Latest doesn't always work
                 .assert()
                 .success();
 
             create_shim_command(sandbox.path(), "python")
                 .arg("--version")
+                .env("PROTO_PYTHON_VERSION", "3.12.0")
                 .assert()
                 .success();
+
+            assert_snapshot!(
+                fs::read_to_string(sandbox.path().join(".proto/shims/registry.json")).unwrap()
+            );
         }
 
         #[test]
         fn supports_rust() {
             let sandbox = create_empty_sandbox();
 
-            let assert = create_proto_command(sandbox.path())
+            create_proto_command(sandbox.path())
                 .arg("install")
                 .arg("rust")
                 .assert();
 
-            starbase_sandbox::debug_process_output(assert.get_output());
-
-            assert.success();
+            // Doesn't create shims
         }
 
         #[test]
@@ -296,6 +330,8 @@ mod plugins {
                 .arg("moon-test")
                 .assert()
                 .success();
+
+            // Doesn't create shims
         }
     }
 }
diff --git a/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_bun.snap b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_bun.snap
new file mode 100644
index 000000000..c9a083b4f
--- /dev/null
+++ b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_bun.snap
@@ -0,0 +1,13 @@
+---
+source: crates/cli/tests/plugins_test.rs
+expression: "fs::read_to_string(sandbox.path().join(\".proto/shims/registry.json\")).unwrap()"
+---
+{
+  "bun": {},
+  "bunx": {
+    "alt_for": "bun",
+    "before_args": [
+      "x"
+    ]
+  }
+}
diff --git a/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_deno.snap b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_deno.snap
new file mode 100644
index 000000000..85e918862
--- /dev/null
+++ b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_deno.snap
@@ -0,0 +1,7 @@
+---
+source: crates/cli/tests/plugins_test.rs
+expression: "fs::read_to_string(sandbox.path().join(\".proto/shims/registry.json\")).unwrap()"
+---
+{
+  "deno": {}
+}
diff --git a/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_go.snap b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_go.snap
new file mode 100644
index 000000000..87c9a8b0d
--- /dev/null
+++ b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_go.snap
@@ -0,0 +1,7 @@
+---
+source: crates/cli/tests/plugins_test.rs
+expression: "fs::read_to_string(sandbox.path().join(\".proto/shims/registry.json\")).unwrap()"
+---
+{
+  "go": {}
+}
diff --git a/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_node.snap b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_node.snap
new file mode 100644
index 000000000..bbb4a6247
--- /dev/null
+++ b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_node.snap
@@ -0,0 +1,7 @@
+---
+source: crates/cli/tests/plugins_test.rs
+expression: "fs::read_to_string(sandbox.path().join(\".proto/shims/registry.json\")).unwrap()"
+---
+{
+  "node": {}
+}
diff --git a/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_npm.snap b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_npm.snap
new file mode 100644
index 000000000..6005a46f2
--- /dev/null
+++ b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_npm.snap
@@ -0,0 +1,14 @@
+---
+source: crates/cli/tests/plugins_test.rs
+expression: "fs::read_to_string(sandbox.path().join(\".proto/shims/registry.json\")).unwrap()"
+---
+{
+  "node": {},
+  "node-gyp": {
+    "alt_for": "npm"
+  },
+  "npm": {},
+  "npx": {
+    "alt_for": "npm"
+  }
+}
diff --git a/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_pnpm.snap b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_pnpm.snap
new file mode 100644
index 000000000..93576adfa
--- /dev/null
+++ b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_pnpm.snap
@@ -0,0 +1,14 @@
+---
+source: crates/cli/tests/plugins_test.rs
+expression: "fs::read_to_string(sandbox.path().join(\".proto/shims/registry.json\")).unwrap()"
+---
+{
+  "node": {},
+  "pnpm": {},
+  "pnpx": {
+    "alt_for": "pnpm",
+    "before_args": [
+      "dlx"
+    ]
+  }
+}
diff --git a/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_python.snap b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_python.snap
new file mode 100644
index 000000000..e1301e890
--- /dev/null
+++ b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_python.snap
@@ -0,0 +1,14 @@
+---
+source: crates/cli/tests/plugins_test.rs
+expression: "fs::read_to_string(sandbox.path().join(\".proto/shims/registry.json\")).unwrap()"
+---
+{
+  "pip": {
+    "alt_for": "python",
+    "before_args": [
+      "-m",
+      "pip"
+    ]
+  },
+  "python": {}
+}
diff --git a/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_yarn.snap b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_yarn.snap
new file mode 100644
index 000000000..0fd8c7bcb
--- /dev/null
+++ b/crates/cli/tests/snapshots/plugins_test__plugins__builtins__supports_yarn.snap
@@ -0,0 +1,11 @@
+---
+source: crates/cli/tests/plugins_test.rs
+expression: "fs::read_to_string(sandbox.path().join(\".proto/shims/registry.json\")).unwrap()"
+---
+{
+  "node": {},
+  "yarn": {},
+  "yarnpkg": {
+    "alt_for": "yarn"
+  }
+}
diff --git a/crates/core/Cargo.toml b/crates/core/Cargo.toml
index 497f859fd..3b199fc2b 100644
--- a/crates/core/Cargo.toml
+++ b/crates/core/Cargo.toml
@@ -34,6 +34,7 @@ semver = { workspace = true }
 serde = { workspace = true }
 serde_json = { workspace = true }
 sha2 = { workspace = true }
+shell-words = { workspace = true }
 starbase_archive = { workspace = true }
 starbase_events = { workspace = true }
 starbase_styles = { workspace = true }
diff --git a/crates/core/src/lib.rs b/crates/core/src/lib.rs
index 069aca845..cd47bcc30 100644
--- a/crates/core/src/lib.rs
+++ b/crates/core/src/lib.rs
@@ -4,6 +4,7 @@ mod helpers;
 mod host_funcs;
 mod proto;
 mod proto_config;
+mod shim_registry;
 mod shimmer;
 mod tool;
 mod tool_loader;
diff --git a/crates/core/src/shim_registry.rs b/crates/core/src/shim_registry.rs
new file mode 100644
index 000000000..f2e9c22cb
--- /dev/null
+++ b/crates/core/src/shim_registry.rs
@@ -0,0 +1,62 @@
+use crate::helpers::{read_json_file_with_lock, write_json_file_with_lock};
+use crate::proto::ProtoEnvironment;
+use serde::{Deserialize, Serialize};
+use std::collections::{BTreeMap, HashMap};
+
+// Keep in sync with crates/cli-shim/src/main.rs
+#[derive(Default, Deserialize, PartialEq, Serialize)]
+#[serde(default)]
+pub struct Shim {
+    #[serde(skip_serializing_if = "Vec::is_empty")]
+    pub after_args: Vec<String>,
+
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub alt_for: Option<String>,
+
+    #[serde(skip_serializing_if = "Vec::is_empty")]
+    pub before_args: Vec<String>,
+
+    #[serde(skip_serializing_if = "HashMap::is_empty")]
+    pub env_vars: HashMap<String, String>,
+}
+
+pub type ShimsMap = BTreeMap<String, Shim>;
+
+pub struct ShimRegistry;
+
+impl ShimRegistry {
+    pub fn update<P: AsRef<ProtoEnvironment>>(proto: P, entries: ShimsMap) -> miette::Result<()> {
+        if entries.is_empty() {
+            return Ok(());
+        }
+
+        let file = proto.as_ref().shims_dir.join("registry.json");
+
+        let mut config: ShimsMap = if file.exists() {
+            read_json_file_with_lock(&file)?
+        } else {
+            BTreeMap::default()
+        };
+
+        let mut mutated = false;
+
+        for (key, value) in entries {
+            // Don't write the file if nothing has changed
+            if config
+                .get(&key)
+                .is_some_and(|current_value| current_value == &value)
+            {
+                continue;
+            }
+
+            config.insert(key, value);
+            mutated = true;
+        }
+
+        if mutated {
+            write_json_file_with_lock(file, &config)?;
+        }
+
+        Ok(())
+    }
+}
diff --git a/crates/core/src/shimmer.rs b/crates/core/src/shimmer.rs
index 21f8d57d7..9a33eed53 100644
--- a/crates/core/src/shimmer.rs
+++ b/crates/core/src/shimmer.rs
@@ -17,10 +17,10 @@ pub struct ShimContext<'tool> {
     pub alt_bin: Option<&'tool str>,
 
     /// Args to prepend to user-provided args.
-    pub before_args: Option<&'tool str>,
+    pub before_args: Option<String>,
 
     /// Args to append to user-provided args.
-    pub after_args: Option<&'tool str>,
+    pub after_args: Option<String>,
 
     // TOOL INFO
     /// ID of the tool, for logging purposes.
diff --git a/crates/core/src/tool.rs b/crates/core/src/tool.rs
index eac155b97..025bd8ce6 100644
--- a/crates/core/src/tool.rs
+++ b/crates/core/src/tool.rs
@@ -7,6 +7,7 @@ use crate::helpers::{
 use crate::host_funcs::{create_host_functions, HostData};
 use crate::proto::ProtoEnvironment;
 use crate::proto_config::ProtoConfig;
+use crate::shim_registry::{Shim, ShimRegistry, ShimsMap};
 use crate::shimmer::{get_shim_file_names, ShimContext, SHIM_VERSION};
 use crate::tool_manifest::{ToolManifest, ToolManifestVersion};
 use crate::version_resolver::VersionResolver;
@@ -1400,23 +1401,58 @@ impl Tool {
             local: vec![],
         };
 
+        let mut registry: ShimsMap = BTreeMap::new();
+        registry.insert(self.id.to_string(), Shim::default());
+
         for location in shims {
+            let mut shim_entry = Shim::default();
             let mut context = self.create_shim_context();
-            context.before_args = location.config.shim_before_args.as_deref();
-            context.after_args = location.config.shim_after_args.as_deref();
 
-            // Only use --alt when the secondary executable exists
-            if !location.primary && location.config.exe_path.is_some() {
-                context.alt_bin = Some(&location.name);
+            // Handle before and after args
+            if let Some(before_args) = &location.config.shim_before_args {
+                context.before_args = Some(before_args.as_string());
+
+                shim_entry.before_args = match before_args {
+                    StringOrVec::String(value) => shell_words::split(value).into_diagnostic()?,
+                    StringOrVec::Vec(value) => value.to_owned(),
+                };
+            }
+
+            if let Some(after_args) = &location.config.shim_after_args {
+                context.after_args = Some(after_args.as_string());
+
+                shim_entry.after_args = match after_args {
+                    StringOrVec::String(value) => shell_words::split(value).into_diagnostic()?,
+                    StringOrVec::Vec(value) => value.to_owned(),
+                };
+            }
+
+            if let Some(env_vars) = &location.config.shim_env_vars {
+                shim_entry.env_vars.extend(env_vars.to_owned());
+            }
+
+            if !location.primary {
+                shim_entry.alt_for = Some(self.id.to_string());
+
+                // Only use --alt when the secondary executable exists
+                if location.config.exe_path.is_some() {
+                    context.alt_bin = Some(&location.name);
+                }
             }
 
             context.create_shim(&location.path, find_only)?;
 
+            // Update the registry
+            registry.insert(location.name.clone(), shim_entry);
+
+            // Add to the event
             event.global.push(location.name);
         }
 
         self.on_created_shims.emit(event).await?;
 
+        ShimRegistry::update(&self.proto, registry)?;
+
         Ok(())
     }
 
diff --git a/crates/core/tests/shimmer_test.rs b/crates/core/tests/shimmer_test.rs
index 97b0a0320..c55ae9291 100644
--- a/crates/core/tests/shimmer_test.rs
+++ b/crates/core/tests/shimmer_test.rs
@@ -52,8 +52,8 @@ mod shimmer {
         let proto = ProtoEnvironment::new_testing(sandbox.path());
 
         let mut context = create_context("primary");
-        context.before_args = Some("--a -b");
-        context.after_args = Some("./file");
+        context.before_args = Some("--a -b".into());
+        context.after_args = Some("./file".into());
 
         let shim_path = proto.shims_dir.join("primary");
         context.create_shim(&shim_path, false).unwrap();
@@ -84,8 +84,8 @@ mod shimmer {
         let bin_path = "other/bin/path";
         let mut context = create_context("primary");
         context.alt_bin = Some(bin_path);
-        context.before_args = Some("--a -b");
-        context.after_args = Some("./file");
+        context.before_args = Some("--a -b".into());
+        context.after_args = Some("./file".into());
 
         let shim_path = proto.shims_dir.join("secondary");
         context.create_shim(&shim_path, false).unwrap();
diff --git a/crates/pdk-api/src/api.rs b/crates/pdk-api/src/api.rs
index 4475ff124..d0fe7005a 100644
--- a/crates/pdk-api/src/api.rs
+++ b/crates/pdk-api/src/api.rs
@@ -1,4 +1,6 @@
 use crate::host_funcs::ExecCommandOutput;
+use crate::shapes::StringOrVec;
+use crate::{json_enum, json_struct};
 use serde::{Deserialize, Serialize};
 use std::collections::HashMap;
 use std::path::PathBuf;
@@ -8,37 +10,10 @@ use warpgate_api::VirtualPath;
 
 pub use semver::{Version, VersionReq};
 
-fn is_empty_map<K, V>(value: &HashMap<K, V>) -> bool {
-    value.is_empty()
-}
-
-fn is_empty_vec<T>(value: &[T]) -> bool {
-    value.is_empty()
-}
-
 fn is_false(value: &bool) -> bool {
     !(*value)
 }
 
-#[doc(hidden)]
-#[macro_export]
-macro_rules! json_struct {
-    ($struct:item) => {
-        #[derive(Clone, Debug, Default, Deserialize, Eq, PartialEq, Serialize)]
-        #[serde(default)]
-        $struct
-    };
-}
-
-#[doc(hidden)]
-#[macro_export]
-macro_rules! json_enum {
-    ($struct:item) => {
-        #[derive(Clone, Debug, Deserialize, Eq, PartialEq, Serialize)]
-        $struct
-    };
-}
-
 json_struct!(
     /// Represents an empty input.
     pub struct EmptyInput {}
@@ -111,7 +86,7 @@ json_struct!(
 
         /// Names of commands that will self-upgrade the tool,
         /// and should be blocked from happening.
-        #[serde(skip_serializing_if = "is_empty_vec")]
+        #[serde(skip_serializing_if = "Vec::is_empty")]
         pub self_upgrade_commands: Vec<String>,
 
         /// Type of the tool.
@@ -126,11 +101,11 @@ json_struct!(
     /// Output returned by the `detect_version_files` function.
     pub struct DetectVersionOutput {
         /// List of files that should be checked for version information.
-        #[serde(skip_serializing_if = "is_empty_vec")]
+        #[serde(skip_serializing_if = "Vec::is_empty")]
         pub files: Vec<String>,
 
         /// List of path patterns to ignore when traversing directories.
-        #[serde(skip_serializing_if = "is_empty_vec")]
+        #[serde(skip_serializing_if = "Vec::is_empty")]
         pub ignore: Vec<String>,
     }
 );
@@ -255,12 +230,12 @@ json_struct!(
 
         /// List of instructions to execute to build the tool, after system
         /// dependencies have been installed.
-        #[serde(skip_serializing_if = "is_empty_vec")]
+        #[serde(skip_serializing_if = "Vec::is_empty")]
         pub instructions: Vec<BuildInstruction>,
 
         /// List of system dependencies that are required for building from source.
         /// If a dependency does not exist, it will be installed.
-        #[serde(skip_serializing_if = "is_empty_vec")]
+        #[serde(skip_serializing_if = "Vec::is_empty")]
         pub system_dependencies: Vec<SystemDependency>,
     }
 );
@@ -387,11 +362,15 @@ json_struct!(
 
         /// Custom args to prepend to user-provided args within the generated shim.
         #[serde(skip_serializing_if = "Option::is_none")]
-        pub shim_before_args: Option<String>,
+        pub shim_before_args: Option<StringOrVec>,
 
         /// Custom args to append to user-provided args within the generated shim.
         #[serde(skip_serializing_if = "Option::is_none")]
-        pub shim_after_args: Option<String>,
+        pub shim_after_args: Option<StringOrVec>,
+
+        /// Custom environment variables to set when executing the shim.
+        #[serde(skip_serializing_if = "Option::is_none")]
+        pub shim_env_vars: Option<HashMap<String, String>>,
     }
 );
 
@@ -417,7 +396,7 @@ json_struct!(
     pub struct LocateExecutablesOutput {
         /// List of directory paths to find the globals installation directory.
         /// Each path supports environment variable expansion.
-        #[serde(skip_serializing_if = "is_empty_vec")]
+        #[serde(skip_serializing_if = "Vec::is_empty")]
         pub globals_lookup_dirs: Vec<String>,
 
         /// A string that all global binaries are prefixed with, and will be removed
@@ -432,7 +411,7 @@ json_struct!(
 
         /// Configures secondary/additional executables to create.
         /// The map key is the name of the shim/binary file.
-        #[serde(skip_serializing_if = "is_empty_map")]
+        #[serde(skip_serializing_if = "HashMap::is_empty")]
         pub secondary: HashMap<String, ExecutableConfig>,
     }
 );
@@ -543,11 +522,11 @@ json_struct!(
         pub latest: Option<Version>,
 
         /// Mapping of aliases (channels, etc) to a version.
-        #[serde(skip_serializing_if = "is_empty_map")]
+        #[serde(skip_serializing_if = "HashMap::is_empty")]
         pub aliases: HashMap<String, Version>,
 
         /// List of available production versions to install.
-        #[serde(skip_serializing_if = "is_empty_vec")]
+        #[serde(skip_serializing_if = "Vec::is_empty")]
         pub versions: Vec<Version>,
     }
 );
diff --git a/crates/pdk-api/src/lib.rs b/crates/pdk-api/src/lib.rs
index ccb23f786..288c8fcb8 100644
--- a/crates/pdk-api/src/lib.rs
+++ b/crates/pdk-api/src/lib.rs
@@ -4,6 +4,7 @@ mod error;
 mod hooks;
 mod host;
 mod host_funcs;
+mod shapes;
 
 pub use api::*;
 pub use api_deprecated::*;
@@ -11,6 +12,7 @@ pub use error::*;
 pub use hooks::*;
 pub use host::*;
 pub use host_funcs::*;
+pub use shapes::*;
 pub use system_env::{DependencyConfig, DependencyName, SystemDependency, SystemPackageManager};
 pub use version_spec::*;
 pub use warpgate_api::*;
diff --git a/crates/pdk-api/src/shapes.rs b/crates/pdk-api/src/shapes.rs
new file mode 100644
index 000000000..e9872f856
--- /dev/null
+++ b/crates/pdk-api/src/shapes.rs
@@ -0,0 +1,37 @@
+use serde::{Deserialize, Serialize};
+
+#[doc(hidden)]
+#[macro_export]
+macro_rules! json_struct {
+    ($struct:item) => {
+        #[derive(Clone, Debug, Default, Deserialize, Eq, PartialEq, Serialize)]
+        #[serde(default)]
+        $struct
+    };
+}
+
+#[doc(hidden)]
+#[macro_export]
+macro_rules! json_enum {
+    ($struct:item) => {
+        #[derive(Clone, Debug, Deserialize, Eq, PartialEq, Serialize)]
+        $struct
+    };
+}
+
+json_enum!(
+    #[serde(untagged)]
+    pub enum StringOrVec {
+        String(String),
+        Vec(Vec<String>),
+    }
+);
+
+impl StringOrVec {
+    pub fn as_string(&self) -> String {
+        match self {
+            Self::String(value) => value.to_owned(),
+            Self::Vec(value) => value.to_vec().join(" "),
+        }
+    }
+}
diff --git a/crates/system-env/Cargo.toml b/crates/system-env/Cargo.toml
index bcd47632a..817e6eee9 100644
--- a/crates/system-env/Cargo.toml
+++ b/crates/system-env/Cargo.toml
@@ -11,7 +11,7 @@ repository = "https://github.com/moonrepo/proto"
 schematic = { workspace = true, optional = true, features = ["schema"] }
 serde = { workspace = true }
 serde_json = { workspace = true }
-shell-words = "1.1.0"
+shell-words = { workspace = true }
 thiserror = { workspace = true }
 
 [features]
diff --git a/plugins/Cargo.lock b/plugins/Cargo.lock
index f802a32c3..0b98988e4 100644
--- a/plugins/Cargo.lock
+++ b/plugins/Cargo.lock
@@ -2184,7 +2184,7 @@ dependencies = [
 
 [[package]]
 name = "proto_core"
-version = "0.24.2"
+version = "0.25.0"
 dependencies = [
  "cached",
  "extism",
@@ -2200,6 +2200,7 @@ dependencies = [
  "serde",
  "serde_json",
  "sha2",
+ "shell-words",
  "starbase_archive",
  "starbase_events",
  "starbase_styles",
@@ -2215,7 +2216,7 @@ dependencies = [
 
 [[package]]
 name = "proto_pdk"
-version = "0.11.1"
+version = "0.11.2"
 dependencies = [
  "anyhow",
  "extism-pdk",
@@ -2225,7 +2226,7 @@ dependencies = [
 
 [[package]]
 name = "proto_pdk_api"
-version = "0.11.1"
+version = "0.11.2"
 dependencies = [
  "anyhow",
  "semver",
@@ -2239,7 +2240,7 @@ dependencies = [
 
 [[package]]
 name = "proto_pdk_test_utils"
-version = "0.12.1"
+version = "0.13.0"
 dependencies = [
  "extism",
  "proto_core",
@@ -2598,9 +2599,9 @@ dependencies = [
 
 [[package]]
 name = "schematic"
-version = "0.12.10"
+version = "0.12.12"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "710a6af816c586a37dc9b8b304370f36d8b90751785bbb245942bed0ae00a69d"
+checksum = "c5ed74b468686fb5551b8f29c8339dcf0b7ac4e0f475490f6f49f6a2aadcd392"
 dependencies = [
  "garde",
  "indexmap 2.1.0",
@@ -2888,9 +2889,9 @@ checksum = "a8f112729512f8e442d81f95a8a7ddf2b7c6b8a1a6f509a95864142b30cab2d3"
 
 [[package]]
 name = "starbase_archive"
-version = "0.2.4"
+version = "0.2.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "935856c30da2f62a73bcc57eecb5508bedd313287bc0e00e7e7c4b7a07fb5995"
+checksum = "b4a0d1c404d4e987597b018bee76fb8e79937f3b2ab0cf5963ce043031092694"
 dependencies = [
  "flate2",
  "miette",
@@ -3549,7 +3550,7 @@ checksum = "49874b5167b65d7193b8aba1567f5c7d93d001cafc34600cee003eda787e483f"
 
 [[package]]
 name = "version_spec"
-version = "0.1.6"
+version = "0.1.7"
 dependencies = [
  "human-sort",
  "regex",
@@ -3588,7 +3589,7 @@ dependencies = [
 
 [[package]]
 name = "warpgate"
-version = "0.6.0"
+version = "0.7.0"
 dependencies = [
  "extism",
  "miette",