diff --git a/api/src/main/java/me/lucko/luckperms/api/context/AbstractContextSet.java b/api/src/main/java/me/lucko/luckperms/api/context/AbstractContextSet.java
index b9c0334c2..03074a359 100644
--- a/api/src/main/java/me/lucko/luckperms/api/context/AbstractContextSet.java
+++ b/api/src/main/java/me/lucko/luckperms/api/context/AbstractContextSet.java
@@ -122,11 +122,33 @@ abstract class AbstractContextSet implements ContextSet {
     }
 
     static String sanitizeKey(String key) {
-        return Objects.requireNonNull(key, "key is null").toLowerCase().intern();
+        Objects.requireNonNull(key, "key is null");
+        if (stringIsEmpty(key)) {
+            throw new IllegalArgumentException("key is (effectively) empty");
+        }
+
+        return key.toLowerCase().intern();
     }
 
     static String sanitizeValue(String value) {
-        return Objects.requireNonNull(value, "value is null").intern();
+        Objects.requireNonNull(value, "value is null");
+        if (stringIsEmpty(value)) {
+            throw new IllegalArgumentException("value is (effectively) empty");
+        }
+
+        return value.intern();
+    }
+
+    private static boolean stringIsEmpty(String s) {
+        if (s.isEmpty()) {
+            return true;
+        }
+        for (char c : s.toCharArray()) {
+            if (c != ' ') {
+                return false;
+            }
+        }
+        return true;
     }
 
 }
diff --git a/api/src/main/java/me/lucko/luckperms/api/context/ContextSet.java b/api/src/main/java/me/lucko/luckperms/api/context/ContextSet.java
index 0ede2d2e1..e4f15fe7a 100644
--- a/api/src/main/java/me/lucko/luckperms/api/context/ContextSet.java
+++ b/api/src/main/java/me/lucko/luckperms/api/context/ContextSet.java
@@ -51,7 +51,9 @@ import javax.annotation.Nonnull;
  * {@link String#toLowerCase() lowercase} by all implementations.
  * Values however are case-sensitive.</p>
  *
- * <p>Context keys and values may not be null.</p>
+ * <p>Context keys and values may not be null or empty. A key/value will be
+ * deemed empty if it's length is zero, or if it consists of only space
+ * characters.</p>
  *
  * <p>Two default ContextSet implementations are provided.
  * {@link MutableContextSet} allows the addition and removal of context keys
diff --git a/common/src/main/java/me/lucko/luckperms/common/commands/utils/ArgumentUtils.java b/common/src/main/java/me/lucko/luckperms/common/commands/utils/ArgumentUtils.java
index 9dc037d5c..5834e7c62 100644
--- a/common/src/main/java/me/lucko/luckperms/common/commands/utils/ArgumentUtils.java
+++ b/common/src/main/java/me/lucko/luckperms/common/commands/utils/ArgumentUtils.java
@@ -134,12 +134,12 @@ public class ArgumentUtils {
                 }
 
                 String key = pair.substring(0, index);
-                if (key.equals("")) {
+                if (key.equals("") || key.trim().isEmpty()) {
                     continue;
                 }
 
                 String value = pair.substring(index + 1);
-                if (value.equals("")) {
+                if (value.equals("") || value.trim().isEmpty()) {
                     continue;
                 }