diff --git a/base/src/resolve.rs b/base/src/resolve.rs
index 0e069a1fed..b5db3b5d67 100644
--- a/base/src/resolve.rs
+++ b/base/src/resolve.rs
@@ -2,7 +2,7 @@ use std::borrow::Cow;
 
 use fnv::FnvMap;
 use symbol::Symbol;
-use types::{AliasData, AliasRef, ArcType, Type, TypeEnv};
+use types::{AliasRef, ArcType, Type, TypeEnv};
 
 quick_error! {
     #[derive(Debug)]
@@ -79,16 +79,22 @@ pub fn remove_aliases_cow<'t>(env: &TypeEnv, typ: &'t ArcType) -> Cow<'t, ArcTyp
     }
 }
 
-pub fn canonical_alias<'t, F>(env: &TypeEnv, typ: &'t ArcType, canonical: F) -> Cow<'t, ArcType>
+/// Resolves aliases until `canonical` returns `true` for an alias in which case it returns the
+/// type that directly contains that alias
+pub fn canonical_alias<'t, F>(env: &TypeEnv, typ: &'t ArcType, mut canonical: F) -> Cow<'t, ArcType>
 where
-    F: Fn(&AliasData<Symbol, ArcType>) -> bool,
+    F: FnMut(&AliasRef<Symbol, ArcType>) -> bool,
 {
     match peek_alias(env, typ) {
-        Ok(Some(alias)) if !canonical(alias) => alias
-            .typ()
-            .apply_args(&typ.unapplied_args())
-            .map(|typ| Cow::Owned(canonical_alias(env, &typ, canonical).into_owned()))
-            .unwrap_or(Cow::Borrowed(typ)),
+        Ok(Some(alias)) => if canonical(alias) {
+            Cow::Borrowed(typ)
+        } else {
+            alias
+                .typ()
+                .apply_args(&typ.unapplied_args())
+                .map(|typ| Cow::Owned(canonical_alias(env, &typ, canonical).into_owned()))
+                .unwrap_or(Cow::Borrowed(typ))
+        },
         _ => Cow::Borrowed(typ),
     }
 }
diff --git a/check/src/typecheck.rs b/check/src/typecheck.rs
index 5ec5f12052..38db8cb053 100644
--- a/check/src/typecheck.rs
+++ b/check/src/typecheck.rs
@@ -433,9 +433,36 @@ impl<'a> Typecheck<'a> {
 
     fn stack_type(&mut self, id: Symbol, alias: &Alias<Symbol, ArcType>) {
         // Insert variant constructors into the local scope
-        let aliased_type = resolve::remove_aliases(&self.environment, alias.typ().into_owned());
-        if let Type::Variant(ref row) = **aliased_type.remove_forall() {
-            for field in row.row_iter().cloned() {
+
+        // We want to prevent the constructors of more specialized aliases from shadowing the more
+        // general ones so we get the canonical alias and then take its inner type without applying
+        // any types to always get the most general type of the constructors
+        //
+        // ```
+        // type Option a = | None | Some a
+        // type OptionInt = Option Int
+        // // Should work
+        // Some ""
+        // ```
+        let aliased_type = alias.typ();
+        let canonical_alias = resolve::canonical_alias(&self.environment, &aliased_type, |alias| {
+            match **alias.unresolved_type().remove_forall() {
+                Type::Variant(_) => true,
+                _ => false,
+            }
+        });
+
+        let canonical_alias = match **canonical_alias.remove_forall() {
+            Type::App(ref func, _) => match **func {
+                Type::Alias(ref alias) => alias.typ(),
+                _ => Cow::Borrowed(func),
+            },
+            Type::Alias(ref alias) => alias.typ(),
+            _ => Cow::Borrowed(canonical_alias.remove_forall()),
+        };
+
+        if let Type::Variant(ref variants) = **canonical_alias {
+            for field in variants.row_iter().cloned() {
                 let symbol = self.symbols.symbol(field.name.as_ref());
                 self.original_symbols.insert(symbol, field.name.clone());
                 self.stack_var(
@@ -444,6 +471,7 @@ impl<'a> Typecheck<'a> {
                 );
             }
         }
+
         let generic_args = alias.params().iter().cloned().map(Type::generic).collect();
         let typ = Type::<_, ArcType>::app(alias.as_ref().clone(), generic_args);
         {
diff --git a/check/tests/pass.rs b/check/tests/pass.rs
index 5001480e15..28875fa1a9 100644
--- a/check/tests/pass.rs
+++ b/check/tests/pass.rs
@@ -566,7 +566,7 @@ Test 1
     let result = support::typecheck(text);
     let expected = Ok(support::typ_a("Test", vec![typ("Int")]));
 
-    assert_eq!(result.map(make_ident_type), expected);
+    assert_req!(result.map(make_ident_type), expected);
 }
 
 #[test]
@@ -644,7 +644,7 @@ in Node { value = 1, tree = Empty } rhs
     let result = support::typecheck(text);
     let expected = Ok(support::typ_a("Tree", vec![typ("Int")]));
 
-    assert_eq!(result.map(make_ident_type), expected);
+    assert_req!(result.map(make_ident_type), expected);
 }
 
 #[test]
@@ -869,3 +869,33 @@ A 1
 
     assert!(result.is_ok(), "{}", result.unwrap_err());
 }
+
+#[test]
+fn dont_shadow_more_generalize_variant_issue_548() {
+    let _ = env_logger::try_init();
+
+    let text = r#"
+type Test a = | Test a
+type TestInt = Test Int
+
+Test ""
+"#;
+    let result = support::typecheck(text);
+
+    assert!(result.is_ok(), "{}", result.unwrap_err());
+}
+
+#[test]
+fn dont_shadow_more_generalize_variant_2_issue_548() {
+    let _ = env_logger::try_init();
+
+    let text = r#"
+type Test a b = | Test a b
+type TestInt b = Test Int b
+
+Test "" 1
+"#;
+    let result = support::typecheck(text);
+
+    assert!(result.is_ok(), "{}", result.unwrap_err());
+}
diff --git a/check/tests/support/mod.rs b/check/tests/support/mod.rs
index e363af6bd1..3008f16751 100644
--- a/check/tests/support/mod.rs
+++ b/check/tests/support/mod.rs
@@ -160,7 +160,6 @@ pub fn typecheck_expr_expected(
     );
     let (_, mut metadata) = metadata::metadata(&env, &expr);
     reparse_infix(&metadata, &*interner, &mut expr).unwrap_or_else(|err| panic!("{}", err));
-    eprintln!("{:?}", expr);
 
     let mut tc = Typecheck::new(
         "test".into(),