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 2fc224cdc..c3cc7d628 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
@@ -2,27 +2,22 @@ package com.github.intellectualsites.plotsquared.plot.commands;
 
 import com.github.intellectualsites.plotsquared.commands.CommandDeclaration;
 import com.github.intellectualsites.plotsquared.plot.PlotSquared;
+import com.github.intellectualsites.plotsquared.plot.config.CaptionUtility;
 import com.github.intellectualsites.plotsquared.plot.config.Captions;
 import com.github.intellectualsites.plotsquared.plot.config.Settings;
-import com.github.intellectualsites.plotsquared.plot.database.DBFunc;
-import com.github.intellectualsites.plotsquared.plot.flag.BlockStateListFlag;
-import com.github.intellectualsites.plotsquared.plot.flag.FlagManager;
-import com.github.intellectualsites.plotsquared.plot.flag.Flags;
+import com.github.intellectualsites.plotsquared.plot.flags.FlagParseException;
 import com.github.intellectualsites.plotsquared.plot.flags.GlobalFlagContainer;
 import com.github.intellectualsites.plotsquared.plot.flags.PlotFlag;
-import com.github.intellectualsites.plotsquared.plot.flags.implementations.PlotWeatherFlag;
-import com.github.intellectualsites.plotsquared.plot.flags.types.BlockTypeListFlag;
 import com.github.intellectualsites.plotsquared.plot.flags.types.IntegerFlag;
+import com.github.intellectualsites.plotsquared.plot.flags.types.ListFlag;
 import com.github.intellectualsites.plotsquared.plot.object.Location;
 import com.github.intellectualsites.plotsquared.plot.object.Plot;
 import com.github.intellectualsites.plotsquared.plot.object.PlotPlayer;
 import com.github.intellectualsites.plotsquared.plot.util.MainUtil;
 import com.github.intellectualsites.plotsquared.plot.util.MathMan;
 import com.github.intellectualsites.plotsquared.plot.util.Permissions;
-import com.github.intellectualsites.plotsquared.plot.util.PlotWeather;
 import com.github.intellectualsites.plotsquared.plot.util.StringComparison;
 import com.github.intellectualsites.plotsquared.plot.util.StringMan;
-import com.sk89q.worldedit.world.block.BlockType;
 
 import java.util.ArrayList;
 import java.util.Arrays;
@@ -32,49 +27,51 @@ import java.util.HashMap;
 import java.util.Iterator;
 import java.util.List;
 import java.util.Map;
-import java.util.Optional;
-import java.util.Set;
+import java.util.StringJoiner;
 
-@CommandDeclaration(command = "setflag", aliases = {"f", "flag",
-    "setflag"}, usage = "/plot flag <set|remove|add|list|info> <flag> <value>", description = "Set plot flags", category = CommandCategory.SETTINGS, requiredType = RequiredType.NONE, permission = "plots.flag")
+@CommandDeclaration(command = "flag", aliases = {"f",
+    "flag"}, usage = "/plot flag <set|remove|add|list|info> <flag> <value>",
+    description = "Set plot flags",
+    category = CommandCategory.SETTINGS,
+    requiredType = RequiredType.NONE,
+    permission = "plots.flag")
 public class FlagCmd extends SubCommand {
 
-    private boolean checkPermValue(PlotPlayer player, PlotFlag<?> flag, String key, String value) {
+    private boolean checkPermValue(PlotPlayer player, PlotFlag<?, ?> flag, String key, String value) {
         key = key.toLowerCase();
         value = value.toLowerCase();
-        String perm = Captions
-            .format(Captions.PERMISSION_SET_FLAG_KEY_VALUE.getTranslated(), key.toLowerCase(),
-                value.toLowerCase());
+        String perm = CaptionUtility
+            .format(Captions.PERMISSION_SET_FLAG_KEY_VALUE.getTranslated(), key.toLowerCase(), value.toLowerCase());
         if (flag instanceof IntegerFlag && MathMan.isInteger(value)) {
             try {
                 int numeric = Integer.parseInt(value);
                 perm = perm.substring(0, perm.length() - value.length() - 1);
                 if (numeric > 0) {
-                    int checkRange = PlotSquared.get().getPlatform().equalsIgnoreCase("bukkit") ?
-                        numeric :
-                        Settings.Limit.MAX_PLOTS;
+                    int checkRange =
+                        PlotSquared.get().getPlatform().equalsIgnoreCase("bukkit") ? numeric : Settings.Limit.MAX_PLOTS;
                     final boolean result = player.hasPermissionRange(perm, checkRange) >= numeric;
                     if (!result) {
-                        MainUtil.sendMessage(player, Captions.NO_PERMISSION, Captions
-                            .format(Captions.PERMISSION_SET_FLAG_KEY_VALUE.getTranslated(),
-                                key.toLowerCase(), value.toLowerCase()));
+                        MainUtil.sendMessage(player, Captions.NO_PERMISSION, CaptionUtility
+                            .format(Captions.PERMISSION_SET_FLAG_KEY_VALUE.getTranslated(), key.toLowerCase(),
+                                value.toLowerCase()));
                     }
                     return result;
                 }
 
             } catch (NumberFormatException ignore) {
             }
-        } else if (flag instanceof BlockTypeListFlag) {
+            // TODO is this required at all?
+        /* } else if (flag instanceof BlockTypeListFlag) {
             final BlockTypeListFlag blockListFlag = (BlockTypeListFlag) flag;
             try {
-                List<BlockType> parsedBlocks = blockListFlag.parse(value);
-                for (final BlockType block : parsedBlocks) {
-                    final String permission = Captions
+                BlockTypeListFlag parsedFlag = blockListFlag.parse(value);
+                for (final BlockType block : parsedFlag.getValue()) {
+                    final String permission = CaptionUtility
                         .format(Captions.PERMISSION_SET_FLAG_KEY_VALUE.getTranslated(),
                             key.toLowerCase(), block.toString().toLowerCase());
                     final boolean result = Permissions.hasPermission(player, permission);
                     if (!result) {
-                        MainUtil.sendMessage(player, Captions.NO_PERMISSION, Captions
+                        MainUtil.sendMessage(player, Captions.NO_PERMISSION, CaptionUtility
                             .format(Captions.PERMISSION_SET_FLAG_KEY_VALUE.getTranslated(),
                                 key.toLowerCase(), value.toLowerCase()));
                         return false;
@@ -83,11 +80,31 @@ public class FlagCmd extends SubCommand {
             } catch (final Exception e) {
                 return false;
             }
+            return true;*/
+        } else if (flag instanceof ListFlag) {
+            final ListFlag<?, ?> listFlag = (ListFlag<?, ?>) flag;
+            try {
+                PlotFlag<? extends List<?>, ?> parsedFlag = listFlag.parse(value);
+                for (final Object entry : parsedFlag.getValue()) {
+                    final String permission = CaptionUtility
+                        .format(Captions.PERMISSION_SET_FLAG_KEY_VALUE.getTranslated(), key.toLowerCase(),
+                            entry.toString().toLowerCase());
+                    final boolean result = Permissions.hasPermission(player, permission);
+                    if (!result) {
+                        MainUtil.sendMessage(player, Captions.NO_PERMISSION, CaptionUtility
+                            .format(Captions.PERMISSION_SET_FLAG_KEY_VALUE.getTranslated(), key.toLowerCase(),
+                                value.toLowerCase()));
+                        return false;
+                    }
+                }
+            } catch (final Exception e) {
+                return false;
+            }
             return true;
         }
         final boolean result = Permissions.hasPermission(player, perm);
         if (!result) {
-            MainUtil.sendMessage(player, Captions.NO_PERMISSION, Captions
+            MainUtil.sendMessage(player, Captions.NO_PERMISSION, CaptionUtility
                 .format(Captions.PERMISSION_SET_FLAG_KEY_VALUE.getTranslated(), key.toLowerCase(),
                     value.toLowerCase()));
         }
@@ -117,20 +134,18 @@ public class FlagCmd extends SubCommand {
             sendMessage(player, Captions.PLOT_NOT_CLAIMED);
             return false;
         }
-        if (!plot.isOwner(player.getUUID()) && !Permissions
-            .hasPermission(player, Captions.PERMISSION_SET_FLAG_OTHER)) {
-            MainUtil
-                .sendMessage(player, Captions.NO_PERMISSION, Captions.PERMISSION_SET_FLAG_OTHER);
+        if (!plot.isOwner(player.getUUID()) && !Permissions.hasPermission(player, Captions.PERMISSION_SET_FLAG_OTHER)) {
+            MainUtil.sendMessage(player, Captions.NO_PERMISSION, Captions.PERMISSION_SET_FLAG_OTHER);
             return false;
         }
-        PlotFlag<?, ?> flag = null;
+        PlotFlag flag = null;
         if (args.length > 1) {
             flag = GlobalFlagContainer.getInstance().getFlagFromString(args[1]);
-            if (flag == null || flag.isReserved()) {
+            if (flag == null) {
                 boolean suggested = false;
                 try {
-                    StringComparison<PlotFlag<?>> stringComparison =
-                        new StringComparison<>(args[1], Flags.getFlags());
+                    StringComparison<PlotFlag<?, ?>> stringComparison =
+                        new StringComparison<>(args[1], GlobalFlagContainer.getInstance().getFlagMap().values());
                     String best = stringComparison.getBestMatch();
                     if (best != null) {
                         MainUtil.sendMessage(player, Captions.NOT_VALID_FLAG_SUGGESTED, best);
@@ -145,106 +160,77 @@ public class FlagCmd extends SubCommand {
         }
         switch (args[0].toLowerCase()) {
             case "info": {
-                if (!Permissions.hasPermission(player, Captions.PERMISSION_SET_FLAG)) {
-                    MainUtil.sendMessage(player, Captions.NO_PERMISSION, "plots.flag.info");
-                    return false;
-                }
-                if (args.length != 2) {
-                    MainUtil.sendMessage(player, Captions.COMMAND_SYNTAX, "/plot flag info <flag>");
-                    return false;
-                }
-                // flag key
-                MainUtil.sendMessage(player, Captions.FLAG_KEY, flag.getName());
-                // flag type
-                MainUtil.sendMessage(player, Captions.FLAG_TYPE, flag.getClass().getSimpleName());
-                // Flag type description
-                MainUtil.sendMessage(player, Captions.FLAG_DESC, flag.getValueDescription());
-                return true;
+                return info(player, args, flag);
             }
             case "set": {
                 if (!Permissions.hasPermission(player, Captions.PERMISSION_SET_FLAG)) {
-                    MainUtil
-                        .sendMessage(player, Captions.NO_PERMISSION, Captions.PERMISSION_SET_FLAG);
+                    MainUtil.sendMessage(player, Captions.NO_PERMISSION, Captions.PERMISSION_SET_FLAG);
                     return false;
                 }
                 if (args.length < 3) {
-                    MainUtil.sendMessage(player, Captions.COMMAND_SYNTAX,
-                        "/plot flag set <flag> <value>");
+                    MainUtil.sendMessage(player, Captions.COMMAND_SYNTAX, "/plot flag set <flag> <value>");
                     return false;
                 }
                 String value = StringMan.join(Arrays.copyOfRange(args, 2, args.length), " ");
                 if (!checkPermValue(player, flag, args[1], value)) {
                     return false;
                 }
-                Object parsed = flag.parseValue(value);
-                if (parsed == null) {
-                    MainUtil.sendMessage(player, "&c" + flag.getValueDescription());
-                    return false;
-                }
-                if (flag instanceof ListFlag) {
-                    if (!(parsed instanceof Collection) || ((Collection) parsed).isEmpty()) {
-                        return !MainUtil.sendMessage(player, Captions.FLAG_NOT_ADDED);
-                    }
-                }
-                boolean result = plot.setFlag(flag, parsed);
-                if (!result) {
-                    MainUtil.sendMessage(player, Captions.FLAG_NOT_ADDED);
+                PlotFlag<?, ?> parsed;
+                try {
+                    parsed = flag.parse(value);
+                } catch (FlagParseException e) {
+                    MainUtil.sendMessage(player, "&c" + e.getErrorMessage());
                     return false;
                 }
+                plot.setFlag(parsed);
                 MainUtil.sendMessage(player, Captions.FLAG_ADDED);
                 return true;
             }
             case "remove": {
                 if (!Permissions.hasPermission(player, Captions.PERMISSION_FLAG_REMOVE)) {
-                    MainUtil.sendMessage(player, Captions.NO_PERMISSION,
-                        Captions.PERMISSION_FLAG_REMOVE);
+                    MainUtil.sendMessage(player, Captions.NO_PERMISSION, Captions.PERMISSION_FLAG_REMOVE);
                     return false;
                 }
                 if (args.length != 2 && args.length != 3) {
-                    MainUtil.sendMessage(player, Captions.COMMAND_SYNTAX,
-                        "/plot flag remove <flag> [values]");
+                    MainUtil.sendMessage(player, Captions.COMMAND_SYNTAX, "/plot flag remove <flag> [values]");
                     return false;
                 }
-                if (!Permissions.hasPermission(player, Captions
-                    .format(Captions.PERMISSION_SET_FLAG_KEY.getTranslated(),
-                        args[1].toLowerCase()))) {
+                if (!Permissions.hasPermission(player,
+                    CaptionUtility.format(Captions.PERMISSION_SET_FLAG_KEY.getTranslated(), args[1].toLowerCase()))) {
                     if (args.length != 3) {
-                        MainUtil.sendMessage(player, Captions.NO_PERMISSION, Captions
-                            .format(Captions.PERMISSION_SET_FLAG_KEY.getTranslated(),
-                                args[1].toLowerCase()));
+                        MainUtil.sendMessage(player, Captions.NO_PERMISSION, CaptionUtility
+                            .format(Captions.PERMISSION_SET_FLAG_KEY.getTranslated(), args[1].toLowerCase()));
                         return false;
                     }
-                    for (String entry : args[2].split(",")) {
-                        if (!checkPermValue(player, flag, args[1], entry)) {
-                            return false;
-                        }
-                    }
                 }
                 if (args.length == 3 && flag instanceof ListFlag) {
                     String value = StringMan.join(Arrays.copyOfRange(args, 2, args.length), " ");
-                    final ListFlag<? extends Collection> listFlag = (ListFlag<? extends Collection>) flag;
-                    final Optional<? extends Collection> collectionOptional = plot.getFlag(listFlag);
-                    if (collectionOptional.isPresent()) {
-                        final Collection parsedCollection = (Collection) flag.parseValue(value);
-                        if (parsedCollection.isEmpty()) {
-                            return !MainUtil.sendMessage(player, Captions.FLAG_NOT_REMOVED);
-                        }
-                        final Collection flagCollection = collectionOptional.get();
-                        if (flagCollection.removeAll(parsedCollection)) {
-                            if (flagCollection.isEmpty()) {
-                                if (plot.removeFlag(flag)) {
-                                    return MainUtil.sendMessage(player, Captions.FLAG_REMOVED);
-                                } else {
-                                    return !MainUtil.sendMessage(player, Captions.FLAG_NOT_REMOVED);
-                                }
+                    final ListFlag<?, ?> listFlag = (ListFlag<?, ?>) flag;
+                    final List<?> list = plot.getFlag((Class<? extends ListFlag<?, ?>>) listFlag.getClass());
+                    final PlotFlag<? extends List<?>, ?> parsedFlag;
+                    try {
+                        parsedFlag = listFlag.parse(value);
+                    } catch (FlagParseException e) {
+                        MainUtil.sendMessage(player, "&c" + e.getErrorMessage());
+                        return false;
+                    }
+                    if (parsedFlag.getValue().isEmpty()) {
+                        return !MainUtil.sendMessage(player, Captions.FLAG_NOT_REMOVED);
+                    }
+                    if (list.removeAll(parsedFlag.getValue())) {
+                        if (list.isEmpty()) {
+                            if (plot.removeFlag(flag)) {
+                                return MainUtil.sendMessage(player, Captions.FLAG_REMOVED);
                             } else {
-                                MainUtil.sendMessage(player, Captions.FLAG_REMOVED);
+                                return !MainUtil.sendMessage(player, Captions.FLAG_NOT_REMOVED);
                             }
                         } else {
-                            return !MainUtil.sendMessage(player, Captions.FLAG_NOT_REMOVED);
+                            MainUtil.sendMessage(player, Captions.FLAG_REMOVED);
                         }
+                    } else {
+                        return !MainUtil.sendMessage(player, Captions.FLAG_NOT_REMOVED);
                     }
-                    DBFunc.setFlags(plot, plot.getFlags());
+                    // TODO reimplement somewhere else: DBFunc.setFlags(plot, plot.getFlags());
                     return true;
                 } else {
                     boolean result = plot.removeFlag(flag);
@@ -253,23 +239,22 @@ public class FlagCmd extends SubCommand {
                         return false;
                     }
                 }
-                if (flag.) {
+                /* TODO reimplement, maybe handle it with events?
+                if (flag == Flags.TIME) {
                     player.setTime(Long.MAX_VALUE);
-                } else if (flag instanceof PlotWeatherFlag) {
+                } else if (flag == Flags.WEATHER) {
                     player.setWeather(PlotWeather.RESET);
-                }
+                }*/
                 MainUtil.sendMessage(player, Captions.FLAG_REMOVED);
                 return true;
             }
             case "add":
                 if (!Permissions.hasPermission(player, Captions.PERMISSION_FLAG_ADD)) {
-                    MainUtil
-                        .sendMessage(player, Captions.NO_PERMISSION, Captions.PERMISSION_FLAG_ADD);
+                    MainUtil.sendMessage(player, Captions.NO_PERMISSION, Captions.PERMISSION_FLAG_ADD);
                     return false;
                 }
                 if (args.length < 3) {
-                    MainUtil.sendMessage(player, Captions.COMMAND_SYNTAX,
-                        "/plot flag add <flag> <values>");
+                    MainUtil.sendMessage(player, Captions.COMMAND_SYNTAX, "/plot flag add <flag> <values>");
                     return false;
                 }
                 for (String entry : args[2].split(",")) {
@@ -278,30 +263,14 @@ public class FlagCmd extends SubCommand {
                     }
                 }
                 String value = StringMan.join(Arrays.copyOfRange(args, 2, args.length), " ");
-                Object parsed = flag.parseValue(value);
-                if (parsed == null) {
-                    MainUtil.sendMessage(player, "&c" + flag.getValueDescription());
+                PlotFlag<?, ?> parsed;
+                try {
+                    parsed = flag.parse(value);
+                } catch (FlagParseException e) {
+                    MainUtil.sendMessage(player, "&c" + flag.getFlagDescription().getTranslated());
                     return false;
                 }
-                Object val = parsed;
-                if (flag instanceof ListFlag) {
-                    final Collection parsedCollection = (Collection<?>) parsed;
-                    if (parsedCollection.isEmpty()) {
-                        return !MainUtil.sendMessage(player, Captions.FLAG_NOT_ADDED);
-                    }
-                    final ListFlag<? extends Collection> listFlag = (ListFlag<? extends Collection>) flag;
-                    final Optional<? extends Collection> collectionOptional = plot.getFlag(listFlag);
-                    if (collectionOptional.isPresent()) {
-                        final Collection flagCollection = collectionOptional.get();
-                        if (flagCollection.addAll(parsedCollection)) {
-                            MainUtil.sendMessage(player, Captions.FLAG_ADDED);
-                            val = flagCollection;
-                        } else {
-                            return !MainUtil.sendMessage(player, Captions.FLAG_NOT_ADDED);
-                        }
-                    }
-                }
-                boolean result = plot.setFlag(flag, val);
+                boolean result = plot.setFlag(flag.merge(parsed.getValue()));
                 if (!result) {
                     MainUtil.sendMessage(player, Captions.FLAG_NOT_ADDED);
                     return false;
@@ -310,8 +279,7 @@ public class FlagCmd extends SubCommand {
                 return true;
             case "list":
                 if (!Permissions.hasPermission(player, Captions.PERMISSION_FLAG_LIST)) {
-                    MainUtil
-                        .sendMessage(player, Captions.NO_PERMISSION, Captions.PERMISSION_FLAG_LIST);
+                    MainUtil.sendMessage(player, Captions.NO_PERMISSION, Captions.PERMISSION_FLAG_LIST);
                     return false;
                 }
                 if (args.length > 1) {
@@ -319,31 +287,43 @@ public class FlagCmd extends SubCommand {
                     return false;
                 }
                 final Map<String, ArrayList<String>> flags = new HashMap<>();
-                for (Flag<?> flag1 : Flags.getFlags()) {
-                    final String category = flag1.getCategoryCaption();
-                    final Collection<String> flagList =
-                        flags.computeIfAbsent(category, k -> new ArrayList<>());
-                    flagList.add(flag1.getName());
+                for (PlotFlag<?, ?> plotFlag : GlobalFlagContainer.getInstance().getRecognizedPlotFlags()) {
+                    final String category = plotFlag.getFlagCategory().getTranslated();
+                    final Collection<String> flagList = flags.computeIfAbsent(category, k -> new ArrayList<>());
+                    flagList.add(plotFlag.getName());
                 }
 
-                final StringBuilder message = new StringBuilder();
-                final Iterator<Map.Entry<String, ArrayList<String>>> iterator =
-                    flags.entrySet().iterator();
+                final Iterator<Map.Entry<String, ArrayList<String>>> iterator = flags.entrySet().iterator();
+                final StringJoiner message = new StringJoiner("\n");
                 while (iterator.hasNext()) {
                     final Map.Entry<String, ArrayList<String>> flagsEntry = iterator.next();
                     final List<String> flagNames = flagsEntry.getValue();
                     Collections.sort(flagNames);
-                    message.append(String.format(Captions.FLAG_LIST_ENTRY.formatted(),
-                        flagsEntry.getKey(), StringMan.join(flagNames, ", ")));
-                    if (iterator.hasNext()) {
-                        message.append("\n");
-                    }
+                    message.add(String.format(Captions.FLAG_LIST_ENTRY.formatted(), flagsEntry.getKey(),
+                        StringMan.join(flagNames, ", ")));
                 }
                 MainUtil.sendMessage(player, message.toString());
                 return true;
         }
-        MainUtil
-            .sendMessage(player, Captions.COMMAND_SYNTAX, getUsage());
+        MainUtil.sendMessage(player, Captions.COMMAND_SYNTAX, getUsage());
         return false;
     }
+
+    private boolean info(PlotPlayer player, String[] args, PlotFlag<?, ?> flag) {
+        if (!Permissions.hasPermission(player, Captions.PERMISSION_SET_FLAG)) {
+            MainUtil.sendMessage(player, Captions.NO_PERMISSION, "plots.flag.info");
+            return false;
+        }
+        if (args.length != 2) {
+            MainUtil.sendMessage(player, Captions.COMMAND_SYNTAX, "/plot flag info <flag>");
+            return false;
+        }
+        // flag key
+        MainUtil.sendMessage(player, Captions.FLAG_KEY, flag.getName());
+        // flag type
+        MainUtil.sendMessage(player, Captions.FLAG_TYPE, flag.getClass().getSimpleName());
+        // Flag type description
+        MainUtil.sendMessage(player, Captions.FLAG_DESC, flag.getFlagDescription().getTranslated());
+        return true;
+    }
 }
diff --git a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/object/Plot.java b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/object/Plot.java
index 59f4979cb..e6018aa39 100644
--- a/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/object/Plot.java
+++ b/Core/src/main/java/com/github/intellectualsites/plotsquared/plot/object/Plot.java
@@ -3157,4 +3157,8 @@ public class Plot {
         return this.flagContainer.getFlag(flagClass).getValue();
     }
 
+    public boolean setFlag(PlotFlag<?, ?> plotFlag) {
+        flagContainer.addFlag(plotFlag);
+        return true;
+    }
 }