diff --git a/src/lib/shell/flow.rs b/src/lib/shell/flow.rs
index 1337fa9b36d7247b9d425f6a65de4cfda11e070e..ff34e7356f64f9aee145ae95a34c970e34d31910 100644
--- a/src/lib/shell/flow.rs
+++ b/src/lib/shell/flow.rs
@@ -492,6 +492,7 @@ impl<'a> Shell<'a> {
     /// Expand an expression and run a branch based on the value of the
     /// expanded expression
     fn execute_match<T: AsRef<str>>(&mut self, expression: T, cases: &[Case<'a>]) -> Result {
+        use regex::RegexSet;
         // Logic for determining if the LHS of a match-case construct (the value we are
         // matching against) matches the RHS of a match-case construct (a value
         // in a case statement). For example, checking to see if the value
@@ -502,13 +503,13 @@ impl<'a> Shell<'a> {
         let is_array = is_array(expression.as_ref());
         let value = self.expand_string(expression.as_ref())?;
         for case in cases.iter() {
-            if case
-                .value
-                .as_ref()
-                .and_then(|v| self.expand_string(v).ok())
-                .filter(|v| v.iter().all(|v| !value.contains(v)))
-                .is_none()
-            {
+            if value.iter().all(|value| {
+                case.value
+                    .as_ref()
+                    .and_then(|v| self.expand_string(v).ok())
+                    .and_then(|v| RegexSet::new(v).ok())
+                    .map_or(false, |regex| regex.is_match(value))
+            }) {
                 // let pattern_is_array = is_array(&value);
                 let previous_bind = case.binding.as_ref().and_then(|bind| {
                     if is_array {
diff --git a/tests/match.ion b/tests/match.ion
index 7c4ecd465dbf197a630bd7cd2d66bce7be44eea3..d2ae63b3afb20f951e8cd3431136ac5c04329e85 100644
--- a/tests/match.ion
+++ b/tests/match.ion
@@ -18,6 +18,16 @@ end
 analyze $out1
 analyze $out2
 
+fn analyze_regex output
+  match output
+    case ".*application/x-gzip"; echo "Use tar -xzf"
+    case _ ; echo "Unknown file type"
+  end
+end
+
+analyze $out1
+analyze $out2
+
 fn wildcard input
   match $input
     case _; echo "WILDCARD!"
diff --git a/tests/match.out b/tests/match.out
index f967baa4009b5fe168adf5e0261b1d11db06d2c1..afc241b29a4dd7c6169a7ed2d2847e0dc5d6e18c 100644
--- a/tests/match.out
+++ b/tests/match.out
@@ -6,6 +6,8 @@ Odd!
 Even!
 Use tar -xzf
 Unknown file type
+Use tar -xzf
+Unknown file type
 WILDCARD!
 WILDCARD!
 Almost half full (or half empty)