diff --git a/cloud-annotations/src/main/java/cloud/commandframework/annotations/Flag.java b/cloud-annotations/src/main/java/cloud/commandframework/annotations/Flag.java
index f0db3de1..0c2cc73c 100644
--- a/cloud-annotations/src/main/java/cloud/commandframework/annotations/Flag.java
+++ b/cloud-annotations/src/main/java/cloud/commandframework/annotations/Flag.java
@@ -88,4 +88,11 @@ public @interface Flag {
      */
     @NonNull String description() default "";
 
+    /**
+     * The flag permission
+     *
+     * @return Flag permission
+     */
+    @NonNull String permission() default "";
+
 }
diff --git a/cloud-annotations/src/main/java/cloud/commandframework/annotations/FlagExtractor.java b/cloud-annotations/src/main/java/cloud/commandframework/annotations/FlagExtractor.java
index 93166c1f..64b01dae 100644
--- a/cloud-annotations/src/main/java/cloud/commandframework/annotations/FlagExtractor.java
+++ b/cloud-annotations/src/main/java/cloud/commandframework/annotations/FlagExtractor.java
@@ -30,6 +30,7 @@ import cloud.commandframework.arguments.flags.CommandFlag;
 import cloud.commandframework.arguments.parser.ArgumentParser;
 import cloud.commandframework.arguments.parser.ParserParameters;
 import cloud.commandframework.arguments.parser.ParserRegistry;
+import cloud.commandframework.permission.Permission;
 import io.leangen.geantyref.TypeToken;
 import org.checkerframework.checker.nullness.qual.NonNull;
 
@@ -61,7 +62,8 @@ final class FlagExtractor implements Function<@NonNull Method, Collection<@NonNu
             final CommandFlag.Builder<Void> builder = this.commandManager
                     .flagBuilder(flag.value())
                     .withDescription(ArgumentDescription.of(flag.description()))
-                    .withAliases(flag.aliases());
+                    .withAliases(flag.aliases())
+                    .withPermission(Permission.of(flag.permission()));
             if (parameter.getType().equals(boolean.class)) {
                 flags.add(builder.build());
             } else {
diff --git a/cloud-core/src/main/java/cloud/commandframework/arguments/compound/FlagArgument.java b/cloud-core/src/main/java/cloud/commandframework/arguments/compound/FlagArgument.java
index 2ca52c2a..7ce8b72e 100644
--- a/cloud-core/src/main/java/cloud/commandframework/arguments/compound/FlagArgument.java
+++ b/cloud-core/src/main/java/cloud/commandframework/arguments/compound/FlagArgument.java
@@ -218,7 +218,7 @@ public final class FlagArgument<C> extends CommandArgument<C, Object> {
                 final List<String> strings = new LinkedList<>();
                 /* Recommend "primary" flags */
                 for (final CommandFlag<?> flag : this.flags) {
-                    if (usedFlags.contains(flag)) {
+                    if (usedFlags.contains(flag) || !commandContext.hasPermission(flag.getCommandPermission())) {
                         continue;
                     }
                     strings.add(
@@ -231,7 +231,7 @@ public final class FlagArgument<C> extends CommandArgument<C, Object> {
                 /* Recommend aliases */
                 final boolean suggestCombined = input.length() > 1 && input.charAt(0) == '-' && input.charAt(1) != '-';
                 for (final CommandFlag<?> flag : this.flags) {
-                    if (usedFlags.contains(flag)) {
+                    if (usedFlags.contains(flag) || !commandContext.hasPermission(flag.getCommandPermission())) {
                         continue;
                     }
                     for (final String alias : flag.getAliases()) {
@@ -279,7 +279,9 @@ public final class FlagArgument<C> extends CommandArgument<C, Object> {
                         }
                     }
                 }
-                if (currentFlag != null && currentFlag.getCommandArgument() != null) {
+                if (currentFlag != null
+                        && commandContext.hasPermission(currentFlag.getCommandPermission())
+                        && currentFlag.getCommandArgument() != null) {
                     return (List<String>) ((BiFunction) currentFlag.getCommandArgument().getSuggestionsProvider())
                             .apply(commandContext, input);
                 }
@@ -394,6 +396,12 @@ public final class FlagArgument<C> extends CommandArgument<C, Object> {
                                     FailureReason.DUPLICATE_FLAG,
                                     commandContext
                             ));
+                        } else if (!commandContext.hasPermission(currentFlag.getCommandPermission())) {
+                            return ArgumentParseResult.failure(new FlagParseException(
+                                    string,
+                                    FailureReason.NO_PERMISSION,
+                                    commandContext
+                            ));
                         }
                         parsedFlags.add(currentFlag);
                         if (currentFlag.getCommandArgument() == null) {
@@ -499,7 +507,8 @@ public final class FlagArgument<C> extends CommandArgument<C, Object> {
         UNKNOWN_FLAG(StandardCaptionKeys.ARGUMENT_PARSE_FAILURE_FLAG_UNKNOWN_FLAG),
         DUPLICATE_FLAG(StandardCaptionKeys.ARGUMENT_PARSE_FAILURE_FLAG_DUPLICATE_FLAG),
         NO_FLAG_STARTED(StandardCaptionKeys.ARGUMENT_PARSE_FAILURE_FLAG_NO_FLAG_STARTED),
-        MISSING_ARGUMENT(StandardCaptionKeys.ARGUMENT_PARSE_FAILURE_FLAG_MISSING_ARGUMENT);
+        MISSING_ARGUMENT(StandardCaptionKeys.ARGUMENT_PARSE_FAILURE_FLAG_MISSING_ARGUMENT),
+        NO_PERMISSION(StandardCaptionKeys.ARGUMENT_PARSE_FAILURE_FLAG_NO_PERMISSION);
 
         private final Caption caption;
 
diff --git a/cloud-core/src/main/java/cloud/commandframework/arguments/flags/CommandFlag.java b/cloud-core/src/main/java/cloud/commandframework/arguments/flags/CommandFlag.java
index 393e6d3b..73258429 100644
--- a/cloud-core/src/main/java/cloud/commandframework/arguments/flags/CommandFlag.java
+++ b/cloud-core/src/main/java/cloud/commandframework/arguments/flags/CommandFlag.java
@@ -25,6 +25,8 @@ package cloud.commandframework.arguments.flags;
 
 import cloud.commandframework.ArgumentDescription;
 import cloud.commandframework.arguments.CommandArgument;
+import cloud.commandframework.permission.CommandPermission;
+import cloud.commandframework.permission.Permission;
 import org.checkerframework.checker.nullness.qual.NonNull;
 import org.checkerframework.checker.nullness.qual.Nullable;
 
@@ -47,6 +49,7 @@ public final class CommandFlag<T> {
     private final @NonNull String name;
     private final @NonNull String @NonNull [] aliases;
     private final @NonNull ArgumentDescription description;
+    private final @NonNull CommandPermission permission;
 
     private final @Nullable CommandArgument<?, T> commandArgument;
 
@@ -54,11 +57,13 @@ public final class CommandFlag<T> {
             final @NonNull String name,
             final @NonNull String @NonNull [] aliases,
             final @NonNull ArgumentDescription description,
+            final @NonNull CommandPermission permission,
             final @Nullable CommandArgument<?, T> commandArgument
     ) {
         this.name = Objects.requireNonNull(name, "name cannot be null");
         this.aliases = Objects.requireNonNull(aliases, "aliases cannot be null");
         this.description = Objects.requireNonNull(description, "description cannot be null");
+        this.permission = Objects.requireNonNull(permission, "permission cannot be null");
         this.commandArgument = commandArgument;
     }
 
@@ -125,6 +130,15 @@ public final class CommandFlag<T> {
         return this.commandArgument;
     }
 
+    /**
+     * Get the command permission, if it exists
+     *
+     * @return Command permission, or {@code null}
+     */
+    public CommandPermission getCommandPermission() {
+        return this.permission;
+    }
+
     @Override
     public String toString() {
         return String.format("--%s", this.name);
@@ -153,22 +167,25 @@ public final class CommandFlag<T> {
         private final String name;
         private final String[] aliases;
         private final ArgumentDescription description;
+        private final CommandPermission permission;
         private final CommandArgument<?, T> commandArgument;
 
         private Builder(
                 final @NonNull String name,
                 final @NonNull String[] aliases,
                 final @NonNull ArgumentDescription description,
+                final @NonNull CommandPermission permission,
                 final @Nullable CommandArgument<?, T> commandArgument
         ) {
             this.name = name;
             this.aliases = aliases;
             this.description = description;
+            this.permission = permission;
             this.commandArgument = commandArgument;
         }
 
         private Builder(final @NonNull String name) {
-            this(name, new String[0], ArgumentDescription.empty(), null);
+            this(name, new String[0], ArgumentDescription.empty(), Permission.empty(), null);
         }
 
         /**
@@ -198,6 +215,7 @@ public final class CommandFlag<T> {
                     this.name,
                     filteredAliases.toArray(new String[0]),
                     this.description,
+                    this.permission,
                     this.commandArgument
             );
         }
@@ -214,7 +232,7 @@ public final class CommandFlag<T> {
             return this.withDescription((ArgumentDescription) description);
         }
 
-        /**d
+        /**
          * Create a new builder instance using the given flag description
          *
          * @param description Flag description
@@ -222,7 +240,7 @@ public final class CommandFlag<T> {
          * @since 1.4.0
          */
         public Builder<T> withDescription(final @NonNull ArgumentDescription description) {
-            return new Builder<>(this.name, this.aliases, description, this.commandArgument);
+            return new Builder<>(this.name, this.aliases, description, this.permission, this.commandArgument);
         }
 
         /**
@@ -233,7 +251,7 @@ public final class CommandFlag<T> {
          * @return New builder instance
          */
         public <N> Builder<N> withArgument(final @NonNull CommandArgument<?, N> argument) {
-            return new Builder<>(this.name, this.aliases, this.description, argument);
+            return new Builder<>(this.name, this.aliases, this.description, this.permission, argument);
         }
 
         /**
@@ -247,13 +265,24 @@ public final class CommandFlag<T> {
             return this.withArgument(builder.build());
         }
 
+        /**
+         * Create a new builder instance using the given flag permission
+         *
+         * @param permission Flag permission
+         * @return New builder instance
+         * @since 1.6.0
+         */
+        public Builder<T> withPermission(final @NonNull CommandPermission permission) {
+            return new Builder<>(this.name, this.aliases, this.description, permission, this.commandArgument);
+        }
+
         /**
          * Build a new command flag instance
          *
          * @return Constructed instance
          */
         public @NonNull CommandFlag<T> build() {
-            return new CommandFlag<>(this.name, this.aliases, this.description, this.commandArgument);
+            return new CommandFlag<>(this.name, this.aliases, this.description, this.permission, this.commandArgument);
         }
 
     }
diff --git a/cloud-core/src/main/java/cloud/commandframework/captions/SimpleCaptionRegistry.java b/cloud-core/src/main/java/cloud/commandframework/captions/SimpleCaptionRegistry.java
index a328c723..634facd5 100644
--- a/cloud-core/src/main/java/cloud/commandframework/captions/SimpleCaptionRegistry.java
+++ b/cloud-core/src/main/java/cloud/commandframework/captions/SimpleCaptionRegistry.java
@@ -80,6 +80,10 @@ public class SimpleCaptionRegistry<C> implements FactoryDelegatingCaptionRegistr
      * Default caption for {@link StandardCaptionKeys#ARGUMENT_PARSE_FAILURE_FLAG_MISSING_ARGUMENT}
      */
     public static final String ARGUMENT_PARSE_FAILURE_FLAG_MISSING_ARGUMENT = "Missing argument for '{flag}'";
+    /**
+     * Default caption for {@link StandardCaptionKeys#ARGUMENT_PARSE_FAILURE_FLAG_NO_PERMISSION}
+     */
+    public static final String ARGUMENT_PARSE_FAILURE_FLAG_NO_PERMISSION = "You don't have permission to use '{flag}'";
     /**
      * Default caption for {@link StandardCaptionKeys#ARGUMENT_PARSE_FAILURE_COLOR}
      */
@@ -132,6 +136,10 @@ public class SimpleCaptionRegistry<C> implements FactoryDelegatingCaptionRegistr
                 StandardCaptionKeys.ARGUMENT_PARSE_FAILURE_FLAG_MISSING_ARGUMENT,
                 (caption, sender) -> ARGUMENT_PARSE_FAILURE_FLAG_MISSING_ARGUMENT
         );
+        this.registerMessageFactory(
+                StandardCaptionKeys.ARGUMENT_PARSE_FAILURE_FLAG_NO_PERMISSION,
+                (caption, sender) -> ARGUMENT_PARSE_FAILURE_FLAG_NO_PERMISSION
+        );
         this.registerMessageFactory(
                 StandardCaptionKeys.ARGUMENT_PARSE_FAILURE_COLOR,
                 (caption, sender) -> ARGUMENT_PARSE_FAILURE_COLOR
diff --git a/cloud-core/src/main/java/cloud/commandframework/captions/StandardCaptionKeys.java b/cloud-core/src/main/java/cloud/commandframework/captions/StandardCaptionKeys.java
index 96060db4..a9584cf2 100644
--- a/cloud-core/src/main/java/cloud/commandframework/captions/StandardCaptionKeys.java
+++ b/cloud-core/src/main/java/cloud/commandframework/captions/StandardCaptionKeys.java
@@ -84,6 +84,10 @@ public final class StandardCaptionKeys {
      * Variables: {flag}
      */
     public static final Caption ARGUMENT_PARSE_FAILURE_FLAG_MISSING_ARGUMENT = of("argument.parse.failure.flag.missing_argument");
+    /**
+     * Variables: {flag}
+     */
+    public static final Caption ARGUMENT_PARSE_FAILURE_FLAG_NO_PERMISSION = of("argument.parse.failure.flag.no_permission");
     /**
      * Variables: {input}
      */
diff --git a/cloud-core/src/main/java/cloud/commandframework/context/CommandContext.java b/cloud-core/src/main/java/cloud/commandframework/context/CommandContext.java
index 2ebeed1c..cbc70e6d 100644
--- a/cloud-core/src/main/java/cloud/commandframework/context/CommandContext.java
+++ b/cloud-core/src/main/java/cloud/commandframework/context/CommandContext.java
@@ -35,6 +35,7 @@ import cloud.commandframework.captions.SimpleCaptionVariableReplacementHandler;
 import cloud.commandframework.keys.CloudKey;
 import cloud.commandframework.keys.CloudKeyHolder;
 import cloud.commandframework.keys.SimpleCloudKey;
+import cloud.commandframework.permission.CommandPermission;
 import org.checkerframework.checker.nullness.qual.NonNull;
 import org.checkerframework.checker.nullness.qual.Nullable;
 
@@ -152,6 +153,27 @@ public final class CommandContext<C> {
         return this.commandSender;
     }
 
+    /**
+     * Check whether the sender that executed the command has a permission.
+     *
+     * @param permission The permission
+     * @return Command sender
+     */
+    public boolean hasPermission(final @NonNull CommandPermission permission) {
+        return this.commandManager.hasPermission(this.commandSender, permission);
+    }
+
+    /**
+     * Check whether the sender that executed the command has a permission.
+     *
+     * @param permission The permission
+     * @return Command sender
+     */
+    public boolean hasPermission(final @NonNull String permission) {
+        return this.commandManager.hasPermission(this.commandSender, permission);
+    }
+
+
     /**
      * Check if this context was created for tab completion purposes
      *