diff --git a/CHANGELOG.md b/CHANGELOG.md
index d67b6017f..6efabd672 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -28,6 +28,15 @@
 #### 🚀 Updates
 
 - Added a `proto migrate v0.24` command for migrating aliases/versions. We'll also log a warning if we detect the old configuration.
+- Updated non-latest plugins to be cached for 30 days, instead of forever.
+
+#### 🐞 Fixes
+
+- Fixed an issue where resolving canary versions wouldn't work correctly.
+
+#### ⚙️ Internal
+
+- We now load and cache the user config, instead of continually loading it.
 
 ## 0.23.2
 
diff --git a/crates/cli/src/commands/migrate/v0_24.rs b/crates/cli/src/commands/migrate/v0_24.rs
index 5ff1d3a03..188d69703 100644
--- a/crates/cli/src/commands/migrate/v0_24.rs
+++ b/crates/cli/src/commands/migrate/v0_24.rs
@@ -30,8 +30,8 @@ pub async fn migrate() -> SystemResult {
             updated_manifest = true;
         }
 
-        if !tool.manifest.default_version.is_some() {
-            debug!("Found a default version");
+        if tool.manifest.default_version.is_some() {
+            debug!("Found default version");
 
             let entry = user_config.tools.entry(tool.id.clone()).or_default();
             entry.default_version = manifest.default_version.take();
diff --git a/crates/cli/src/commands/run.rs b/crates/cli/src/commands/run.rs
index a139263ad..5777ffc7a 100644
--- a/crates/cli/src/commands/run.rs
+++ b/crates/cli/src/commands/run.rs
@@ -154,9 +154,7 @@ pub async fn run(args: ArgsRef<RunArgs>) -> SystemResult {
 
     // Check if installed or install
     if !tool.is_setup(&version).await? {
-        let user_config = tool.proto.load_user_config()?;
-
-        if !user_config.auto_install {
+        if !tool.proto.load_user_config()?.auto_install {
             return Err(ProtoError::MissingToolForRun {
                 tool: tool.get_name().to_owned(),
                 version: version.to_string(),
diff --git a/crates/cli/src/commands/tool/list.rs b/crates/cli/src/commands/tool/list.rs
index 04f82d0ee..2e4d67814 100644
--- a/crates/cli/src/commands/tool/list.rs
+++ b/crates/cli/src/commands/tool/list.rs
@@ -53,13 +53,13 @@ pub async fn list(args: ArgsRef<ListToolsArgs>) {
             .map(|t| {
                 let user_config = user_config.tools.remove(&t.id);
 
-                return (
+                (
                     t.id,
                     ToolItem {
                         manifest: t.manifest,
                         user_config,
                     },
-                );
+                )
             })
             .collect::<HashMap<_, _>>();
 
diff --git a/crates/core/tests/version_resolver_test.rs b/crates/core/tests/version_resolver_test.rs
index 53445ac39..42fdb4a84 100644
--- a/crates/core/tests/version_resolver_test.rs
+++ b/crates/core/tests/version_resolver_test.rs
@@ -1,4 +1,6 @@
-use proto_core::{resolve_version, ToolManifest, UnresolvedVersionSpec, VersionSpec};
+use proto_core::{
+    resolve_version, ToolManifest, UnresolvedVersionSpec, UserToolConfig, VersionSpec,
+};
 use semver::Version;
 use std::collections::BTreeMap;
 
@@ -43,15 +45,6 @@ mod version_resolver {
     fn create_manifest() -> ToolManifest {
         let mut manifest = ToolManifest::default();
 
-        manifest.aliases.insert(
-            "latest-manifest".into(),
-            UnresolvedVersionSpec::Version(Version::new(8, 0, 0)),
-        );
-        manifest.aliases.insert(
-            "stable-manifest".into(),
-            UnresolvedVersionSpec::Alias("stable".into()),
-        );
-
         manifest
             .installed_versions
             .insert(VersionSpec::parse("3.0.0").unwrap());
@@ -62,6 +55,21 @@ mod version_resolver {
         manifest
     }
 
+    fn create_tool_config() -> UserToolConfig {
+        let mut config = UserToolConfig::default();
+
+        config.aliases.insert(
+            "latest-manifest".into(),
+            UnresolvedVersionSpec::Version(Version::new(8, 0, 0)),
+        );
+        config.aliases.insert(
+            "stable-manifest".into(),
+            UnresolvedVersionSpec::Alias("stable".into()),
+        );
+
+        config
+    }
+
     #[test]
     fn resolves_aliases() {
         let versions = create_versions();
@@ -93,10 +101,11 @@ mod version_resolver {
     }
 
     #[test]
-    fn resolves_aliases_from_manifest() {
+    fn resolves_aliases_from_config() {
         let versions = create_versions();
         let aliases = create_aliases();
         let manifest = create_manifest();
+        let config = create_tool_config();
 
         assert_eq!(
             resolve_version(
@@ -104,7 +113,7 @@ mod version_resolver {
                 &versions,
                 &aliases,
                 Some(&manifest),
-                None,
+                Some(&config),
             )
             .unwrap(),
             Version::new(8, 0, 0)
@@ -116,7 +125,7 @@ mod version_resolver {
                 &versions,
                 &aliases,
                 Some(&manifest),
-                None,
+                Some(&config),
             )
             .unwrap(),
             Version::new(10, 0, 0)
@@ -202,10 +211,11 @@ mod version_resolver {
     }
 
     #[test]
-    fn resolves_versions_from_manifest() {
+    fn resolves_versions_from_config() {
         let versions = create_versions();
         let aliases = create_aliases();
         let manifest = create_manifest();
+        let config = create_tool_config();
 
         assert_eq!(
             resolve_version(
@@ -213,7 +223,7 @@ mod version_resolver {
                 &versions,
                 &aliases,
                 Some(&manifest),
-                None,
+                Some(&config),
             )
             .unwrap(),
             Version::new(3, 0, 0)
@@ -263,10 +273,11 @@ mod version_resolver {
     }
 
     #[test]
-    fn resolves_partial_versions_with_manifest() {
+    fn resolves_partial_versions_with_config() {
         let versions = create_versions();
         let aliases = create_aliases();
         let manifest = create_manifest();
+        let config = create_tool_config();
 
         assert_eq!(
             resolve_version(
@@ -274,7 +285,7 @@ mod version_resolver {
                 &versions,
                 &aliases,
                 Some(&manifest),
-                None,
+                Some(&config),
             )
             .unwrap(),
             Version::new(3, 3, 3)
@@ -286,7 +297,7 @@ mod version_resolver {
                 &versions,
                 &aliases,
                 Some(&manifest),
-                None,
+                Some(&config),
             )
             .unwrap(),
             Version::new(3, 3, 3)
diff --git a/crates/warpgate/src/loader.rs b/crates/warpgate/src/loader.rs
index 0204e4c09..d1b70e596 100644
--- a/crates/warpgate/src/loader.rs
+++ b/crates/warpgate/src/loader.rs
@@ -140,25 +140,26 @@ impl PluginLoader {
             return Ok(false);
         }
 
-        let mut cached = true;
+        let metadata = fs::metadata(path)?;
 
-        // If latest, cache only lasts for 7 days
-        if fs::file_name(path).contains("-latest-") {
-            let metadata = fs::metadata(path)?;
-
-            cached = if let Ok(filetime) = metadata.created().or_else(|_| metadata.modified()) {
-                filetime > SystemTime::now() - Duration::from_secs(86400 * 7)
+        let mut cached = if let Ok(filetime) = metadata.created().or_else(|_| metadata.modified()) {
+            let days = if fs::file_name(path).contains("-latest-") {
+                7
             } else {
-                false
+                30
             };
 
-            if !cached && self.is_offline() {
-                cached = true;
-            }
+            filetime > SystemTime::now() - Duration::from_secs(86400 * days)
+        } else {
+            false
+        };
 
-            if !cached {
-                fs::remove_file(path)?;
-            }
+        if !cached && self.is_offline() {
+            cached = true;
+        }
+
+        if !cached {
+            fs::remove_file(path)?;
         }
 
         if cached {