diff --git a/Essentials/src/main/java/com/earth2me/essentials/ISettings.java b/Essentials/src/main/java/com/earth2me/essentials/ISettings.java
index 13cfeff48..15a2ef450 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/ISettings.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/ISettings.java
@@ -345,7 +345,7 @@ public interface ISettings extends IConf {
 
     boolean isConfirmCommandEnabledByDefault(String commandName);
 
-    boolean isTeleportBackWhenFreedFromJail();
+    TeleportWhenFreePolicy getTeleportWhenFreePolicy();
 
     boolean isJailOnlineTime();
 
@@ -385,4 +385,10 @@ public interface ISettings extends IConf {
         DROP
     }
 
+    enum TeleportWhenFreePolicy {
+        SPAWN,
+        BACK,
+        OFF
+    }
+
 }
diff --git a/Essentials/src/main/java/com/earth2me/essentials/Settings.java b/Essentials/src/main/java/com/earth2me/essentials/Settings.java
index 4efe62276..da2591d52 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/Settings.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/Settings.java
@@ -122,7 +122,7 @@ public class Settings implements net.ess3.api.ISettings {
     private NumberFormat currencyFormat;
     private List<EssentialsSign> unprotectedSigns = Collections.emptyList();
     private List<String> defaultEnabledConfirmCommands;
-    private boolean teleportBackWhenFreedFromJail;
+    private TeleportWhenFreePolicy teleportWhenFreePolicy;
     private boolean isCompassTowardsHomePerm;
     private boolean isAllowWorldInBroadcastworld;
     private String itemDbType; // #EasterEgg - admins can manually switch items provider if they want
@@ -724,7 +724,7 @@ public class Settings implements net.ess3.api.ISettings {
         currencyFormat = _getCurrencyFormat();
         unprotectedSigns = _getUnprotectedSign();
         defaultEnabledConfirmCommands = _getDefaultEnabledConfirmCommands();
-        teleportBackWhenFreedFromJail = _isTeleportBackWhenFreedFromJail();
+        teleportWhenFreePolicy = _getTeleportWhenFreePolicy();
         isCompassTowardsHomePerm = _isCompassTowardsHomePerm();
         isAllowWorldInBroadcastworld = _isAllowWorldInBroadcastworld();
         itemDbType = _getItemDbType();
@@ -1703,13 +1703,27 @@ public class Settings implements net.ess3.api.ISettings {
         return getDefaultEnabledConfirmCommands().contains(commandName.toLowerCase());
     }
 
-    private boolean _isTeleportBackWhenFreedFromJail() {
-        return config.getBoolean("teleport-back-when-freed-from-jail", true);
+    private TeleportWhenFreePolicy _getTeleportWhenFreePolicy() {
+        if (config.hasProperty("teleport-back-when-freed-from-jail")) {
+            return config.getBoolean("teleport-back-when-freed-from-jail", true) ? TeleportWhenFreePolicy.BACK : TeleportWhenFreePolicy.OFF;
+        }
+
+        if (config.hasProperty("teleport-when-freed")) {
+            // snakeyaml more like cursedyaml
+            final String value = config.getString("teleport-when-freed", "back").replace("false", "off");
+            try {
+                return TeleportWhenFreePolicy.valueOf(value.toUpperCase(Locale.ROOT));
+            } catch (IllegalArgumentException e) {
+                throw new RuntimeException("Invalid value \"" + value + "\" for config option \"teleport-when-freed\"!", e);
+            }
+        }
+
+        return TeleportWhenFreePolicy.BACK;
     }
 
     @Override
-    public boolean isTeleportBackWhenFreedFromJail() {
-        return teleportBackWhenFreedFromJail;
+    public TeleportWhenFreePolicy getTeleportWhenFreePolicy() {
+        return teleportWhenFreePolicy;
     }
 
     @Override
diff --git a/Essentials/src/main/java/com/earth2me/essentials/User.java b/Essentials/src/main/java/com/earth2me/essentials/User.java
index 9f8bc1b4a..ee59394eb 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/User.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/User.java
@@ -649,13 +649,15 @@ public class User extends UserData implements Comparable<User>, IMessageRecipien
                     setJailed(false);
                     sendMessage(tl("haveBeenReleased"));
                     setJail(null);
-                    if (ess.getSettings().isTeleportBackWhenFreedFromJail()) {
+                    if (ess.getSettings().getTeleportWhenFreePolicy() == ISettings.TeleportWhenFreePolicy.BACK) {
                         final CompletableFuture<Boolean> future = new CompletableFuture<>();
                         getAsyncTeleport().back(future);
                         future.exceptionally(e -> {
                             getAsyncTeleport().respawn(null, TeleportCause.PLUGIN, new CompletableFuture<>());
                             return false;
                         });
+                    } else if (ess.getSettings().getTeleportWhenFreePolicy() == ISettings.TeleportWhenFreePolicy.SPAWN) {
+                        getAsyncTeleport().respawn(null, TeleportCause.PLUGIN, new CompletableFuture<>());
                     }
                     return true;
                 }
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtogglejail.java b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtogglejail.java
index 815082640..93a7128f1 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtogglejail.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtogglejail.java
@@ -1,6 +1,7 @@
 package com.earth2me.essentials.commands;
 
 import com.earth2me.essentials.CommandSource;
+import com.earth2me.essentials.ISettings;
 import com.earth2me.essentials.User;
 import com.earth2me.essentials.utils.DateUtil;
 import com.earth2me.essentials.utils.EnumUtil;
@@ -122,19 +123,23 @@ public class Commandtogglejail extends EssentialsCommand {
                 player.setJailTimeout(0);
                 player.sendMessage(tl("jailReleasedPlayerNotify"));
                 player.setJail(null);
-                if (player.getBase().isOnline() && ess.getSettings().isTeleportBackWhenFreedFromJail()) {
+                if (player.getBase().isOnline()) {
                     final CompletableFuture<Boolean> future = getNewExceptionFuture(sender, commandLabel);
-                    player.getAsyncTeleport().back(future);
                     future.thenAccept(success -> {
                         if (success) {
                             sender.sendMessage(tl("jailReleased", player.getName()));
                         }
                     });
-                    future.exceptionally(e -> {
-                        player.getAsyncTeleport().respawn(null, PlayerTeleportEvent.TeleportCause.PLUGIN, new CompletableFuture<>());
-                        sender.sendMessage(tl("jailReleased", player.getName()));
-                        return false;
-                    });
+                    if (ess.getSettings().getTeleportWhenFreePolicy() == ISettings.TeleportWhenFreePolicy.BACK) {
+                        player.getAsyncTeleport().back(future);
+                        future.exceptionally(e -> {
+                            player.getAsyncTeleport().respawn(null, PlayerTeleportEvent.TeleportCause.PLUGIN, new CompletableFuture<>());
+                            sender.sendMessage(tl("jailReleased", player.getName()));
+                            return false;
+                        });
+                    } else if (ess.getSettings().getTeleportWhenFreePolicy() == ISettings.TeleportWhenFreePolicy.SPAWN) {
+                        player.getAsyncTeleport().respawn(null, PlayerTeleportEvent.TeleportCause.PLUGIN, future);
+                    }
                     return;
                 }
                 sender.sendMessage(tl("jailReleased", player.getName()));
diff --git a/Essentials/src/main/resources/config.yml b/Essentials/src/main/resources/config.yml
index c9b01966b..555e9646c 100644
--- a/Essentials/src/main/resources/config.yml
+++ b/Essentials/src/main/resources/config.yml
@@ -644,8 +644,10 @@ default-enabled-confirm-commands:
 #- pay
 #- clearinventory
 
-# Whether or not to teleport a player back to their previous position after they have been freed from jail.
-teleport-back-when-freed-from-jail: true
+# Where should Essentials teleport players when they are freed from jail?
+# You can set to "back" to have them teleported to where they were before they were jailed, "spawn" to have them
+# teleport to spawn, or "off" to not have them teleport.
+teleport-when-freed: back
 
 # Whether or not jail time should only be counted while the user is online.
 # If true, a jailed player's time will only decrement when they are online.