diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/commands/FlagCmd.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/commands/FlagCmd.java
index 833c0b780..35888fdde 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/commands/FlagCmd.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/commands/FlagCmd.java
@@ -293,11 +293,12 @@ public class FlagCmd extends SubCommand {
                     MainUtil.sendMessage(player, Captions.COMMAND_SYNTAX, "/plot flag list");
                     return false;
                 }
-                HashMap<String, ArrayList<String>> flags = new HashMap<>();
+                final Map<String, ArrayList<String>> flags = new HashMap<>();
                 for (Flag<?> flag1 : Flags.getFlags()) {
-                    String type = flag1.getClass().getSimpleName();
-                    flags.computeIfAbsent(type, k -> new ArrayList<>());
-                    flags.get(type).add(flag1.getName());
+                    final String category = flag1.getCategoryCaption();
+                    final Collection<String> flagList =
+                        flags.computeIfAbsent(category, k -> new ArrayList<>());
+                    flagList.add(flag1.getName());
                 }
                 StringBuilder message = new StringBuilder();
                 String prefix = "";
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/config/Captions.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/config/Captions.java
index 35538a637..d0e386ea3 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/config/Captions.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/config/Captions.java
@@ -567,9 +567,7 @@ public enum Captions {
     //</editor-fold>
     BUCKET_ENTRIES_IGNORED("$2Total bucket values add up to 1 or more. Blocks without a specified chance will be ignored","Generator_Bucket"),
 
-    /**
-     * Command Categories
-     */
+    //<editor-fold desc="Command Categories">
     COMMAND_CATEGORY_CLAIMING("Claiming", "Category"),
     COMMAND_CATEGORY_TELEPORT("Teleport", "Category"),
     COMMAND_CATEGORY_SETTINGS("Protection", "Category"),
@@ -579,6 +577,7 @@ public enum Captions {
     COMMAND_CATEGORY_INFO("Info", "Category"),
     COMMAND_CATEGORY_DEBUG("Debug", "Category"),
     COMMAND_CATEGORY_ADMINISTRATION("Admin", "Category"),
+    //</editor-fold>
 
     //<editor-fold desc="Grants">
     GRANTED_PLOTS("$1Result: $2%s $1grants left", "Grants"),
@@ -586,6 +585,22 @@ public enum Captions {
     GRANTED_PLOT_FAILED("$1Grant failed: $2%s", "Grants"),
     //</editor-fold>
 
+    //<editor-fold desc="Flag category captions">
+    FLAG_CATEGORY_STRING("String Flags", "Flags"),
+    FLAG_CATEGORY_INTEGERS("Integer Flags", "Flags"),
+    FLAG_CATEGORY_TELEPORT_DENY("Teleport Deny Flag", "Flags"),
+    FLAG_CATEGORY_STRING_LIST("String List Flags", "Flags"),
+    FLAG_CATEGORY_WEATHER("Weather Flags", "Flags"),
+    FLAG_CATEGORY_BLOCK_LIST("Material Flags", "Flags"),
+    FLAG_CATEGORY_INTERVALS("Interval Flags", "Flags"),
+    FLAG_CATEGORY_INTEGER_LIST("Integer List Flags", "Flags"),
+    FLAG_CATEGORY_GAMEMODE("Game Mode Flags", "Flags"),
+    FLAG_CATEGORY_ENUM("Generic Enum Flags", "Flags"),
+    FLAG_CATEGORY_DECIMAL("Decimal Flags", "Flags"),
+    FLAG_CATEGORY_BOOLEAN("Boolean Flags", "Flags"),
+    FLAG_CATEGORY_MIXED("Mixed Value Flags", "Flags"),
+    //</editor-fold>
+
     /**
      * Legacy Configuration Conversion
      */
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/BooleanFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/BooleanFlag.java
index a492c9c0f..841df766c 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/BooleanFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/BooleanFlag.java
@@ -1,11 +1,12 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.object.Plot;
 
 public class BooleanFlag extends Flag<Boolean> {
 
     public BooleanFlag(String name) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_BOOLEAN, name);
     }
 
     @Override public String valueToString(Object value) {
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/DoubleFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/DoubleFlag.java
index 9b46a2cde..8cc665471 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/DoubleFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/DoubleFlag.java
@@ -1,9 +1,11 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
+
 public class DoubleFlag extends Flag<Double> {
 
     public DoubleFlag(String name) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_DECIMAL, name);
     }
 
     @Override public String valueToString(Object value) {
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/EnumFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/EnumFlag.java
index 3ba6b2457..88119bbaa 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/EnumFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/EnumFlag.java
@@ -1,15 +1,17 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.util.StringMan;
 
 import java.util.Arrays;
 import java.util.HashSet;
 
 public class EnumFlag extends Flag<String> {
+
     private final HashSet<String> values;
 
     public EnumFlag(String name, String... values) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_ENUM, name);
         this.values = new HashSet<>(Arrays.asList(values));
     }
 
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/Flag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/Flag.java
index 3b247d87a..21047d9cd 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/Flag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/Flag.java
@@ -1,13 +1,21 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.object.Plot;
 import com.github.intellectualsites.plotsquared.plot.util.StringComparison;
+import lombok.Getter;
 
 public abstract class Flag<V> implements StringComparison.StringComparable {
 
+    @Getter private final Captions typeCaption;
     private final String name;
     private boolean reserved = false;
 
+    public Flag(Captions typeCaption, String name) {
+        this.typeCaption = typeCaption;
+        this.name = name;
+    }
+
     /**
      * Flag object used to store basic information for a Plot. Flags are a
      * key/value pair. For a flag to be usable by a player, you need to
@@ -16,7 +24,7 @@ public abstract class Flag<V> implements StringComparison.StringComparable {
      * @param name the flag name
      */
     public Flag(String name) {
-        this.name = name;
+        this(null, name);
     }
 
     public Flag<V> reserve() {
@@ -57,4 +65,11 @@ public abstract class Flag<V> implements StringComparison.StringComparable {
     @Override public String getComparableString() {
         return getName();
     }
+
+    public String getCategoryCaption() {
+        return this.typeCaption == null ?
+               getClass().getSimpleName() :
+               this.typeCaption.getTranslated();
+    }
+
 }
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/Flags.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/Flags.java
index fc203a00b..ed5560f09 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/Flags.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/Flags.java
@@ -1,6 +1,7 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
 import com.github.intellectualsites.plotsquared.plot.PlotSquared;
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.util.MainUtil;
 import com.github.intellectualsites.plotsquared.plot.util.MathMan;
 import com.github.intellectualsites.plotsquared.plot.util.StringMan;
@@ -95,7 +96,7 @@ public final class Flags {
     public static final IntegerFlag ANIMAL_CAP = new IntegerFlag("animal-cap");
     public static final IntegerFlag HOSTILE_CAP = new IntegerFlag("hostile-cap");
     public static final IntegerFlag VEHICLE_CAP = new IntegerFlag("vehicle-cap");
-    public static final Flag<?> KEEP = new Flag("keep") {
+    public static final Flag<?> KEEP = new Flag(Captions.FLAG_CATEGORY_MIXED, "keep") {
         @Override public String valueToString(Object value) {
             return value.toString();
         }
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/GameModeFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/GameModeFlag.java
index 80225c2aa..26510b35b 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/GameModeFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/GameModeFlag.java
@@ -1,11 +1,12 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.util.PlotGameMode;
 
 public class GameModeFlag extends Flag<PlotGameMode> {
 
     public GameModeFlag(String name) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_GAMEMODE, name);
     }
 
     @Override public String valueToString(Object value) {
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntegerFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntegerFlag.java
index 2cafed4d1..ced532cd1 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntegerFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntegerFlag.java
@@ -1,11 +1,12 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.object.Plot;
 
 public class IntegerFlag extends Flag<Integer> {
 
     public IntegerFlag(String name) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_INTEGERS, name);
     }
 
     @Override public String getValueDescription() {
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntegerListFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntegerListFlag.java
index e46071b86..1f24cb4a3 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntegerListFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntegerListFlag.java
@@ -1,5 +1,6 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.util.StringMan;
 
 import java.util.ArrayList;
@@ -9,7 +10,7 @@ import java.util.List;
 public class IntegerListFlag extends ListFlag<List<Integer>> {
 
     public IntegerListFlag(String name) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_INTEGER_LIST, name);
     }
 
     @Override public String valueToString(Object value) {
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntervalFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntervalFlag.java
index c8f490591..0468c59b2 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntervalFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/IntervalFlag.java
@@ -1,5 +1,6 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import lombok.EqualsAndHashCode;
 import lombok.Getter;
 import lombok.RequiredArgsConstructor;
@@ -7,7 +8,7 @@ import lombok.RequiredArgsConstructor;
 public class IntervalFlag extends Flag<IntervalFlag.Interval> {
 
     public IntervalFlag(String name) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_INTERVALS, name);
     }
 
     @Override public String valueToString(Object value) {
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/ListFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/ListFlag.java
index 518c3df11..3085288b1 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/ListFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/ListFlag.java
@@ -1,11 +1,16 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.object.Plot;
 
 import java.util.Collection;
 
 public abstract class ListFlag<V extends Collection<?>> extends Flag<V> {
 
+    public ListFlag(Captions typeCaption, String name) {
+        super(typeCaption, name);
+    }
+
     public ListFlag(String name) {
         super(name);
     }
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/LongFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/LongFlag.java
index 464780af8..8d57e8865 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/LongFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/LongFlag.java
@@ -1,9 +1,11 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
+
 public class LongFlag extends Flag<Long> {
 
     public LongFlag(String name) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_INTEGERS, name);
     }
 
     @Override public Long parseValue(String value) {
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/PlotBlockListFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/PlotBlockListFlag.java
index 4be8ac475..93bd8c56f 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/PlotBlockListFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/PlotBlockListFlag.java
@@ -1,6 +1,7 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
 import com.github.intellectualsites.plotsquared.plot.PlotSquared;
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.object.PlotBlock;
 import com.github.intellectualsites.plotsquared.plot.util.LegacyMappings;
 import com.github.intellectualsites.plotsquared.plot.util.StringMan;
@@ -14,7 +15,7 @@ import java.util.stream.Collectors;
 public class PlotBlockListFlag extends ListFlag<HashSet<PlotBlock>> {
 
     public PlotBlockListFlag(String name) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_BLOCK_LIST, name);
     }
 
     @Override public String valueToString(Object value) {
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/PlotWeatherFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/PlotWeatherFlag.java
index e6f93ee2d..43544748f 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/PlotWeatherFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/PlotWeatherFlag.java
@@ -1,11 +1,12 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.util.PlotWeather;
 
 public class PlotWeatherFlag extends Flag<PlotWeather> {
 
     public PlotWeatherFlag(String name) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_WEATHER, name);
     }
 
     @Override public String valueToString(Object value) {
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/StringFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/StringFlag.java
index 36a68f66b..6438ec938 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/StringFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/StringFlag.java
@@ -1,10 +1,12 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
+
 public class StringFlag extends Flag<String> {
 
     public StringFlag(String name) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_STRING, name);
     }
 
     @Override public String valueToString(Object value) {
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/StringListFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/StringListFlag.java
index 8f02a3801..a1e28aa3d 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/StringListFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/StringListFlag.java
@@ -1,5 +1,6 @@
 package com.github.intellectualsites.plotsquared.plot.flag;
 
+import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.util.StringMan;
 
 import java.util.ArrayList;
@@ -9,7 +10,7 @@ import java.util.List;
 public class StringListFlag extends ListFlag<List<String>> {
 
     public StringListFlag(String name) {
-        super(name);
+        super(Captions.FLAG_CATEGORY_STRING_LIST, name);
     }
 
     @Override public String valueToString(Object value) {
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/TeleportDenyFlag.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/TeleportDenyFlag.java
index 90f6c292c..6c02516fd 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/TeleportDenyFlag.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/flag/TeleportDenyFlag.java
@@ -4,6 +4,7 @@ import com.github.intellectualsites.plotsquared.plot.object.Plot;
 import com.github.intellectualsites.plotsquared.plot.object.PlotPlayer;
 
 public class TeleportDenyFlag extends EnumFlag {
+
     public TeleportDenyFlag(String name) {
         super(name, "trusted", "members", "nonmembers", "nontrusted", "nonowners");
     }