diff --git a/expcore/roles.lua b/expcore/roles.lua
index 2028cd23..b6d1000d 100644
--- a/expcore/roles.lua
+++ b/expcore/roles.lua
@@ -115,6 +115,7 @@ local Groups = require 'expcore.permission_groups' --- @dep expcore.permission_g
 local Async = require 'expcore.async' --- @dep expcore.async
 local Colours = require 'utils.color_presets' --- @dep utils.color_presets
 local write_json = _C.write_json --- @dep expcore.common
+local JailOldRole = require 'modules.control.jail_old_role' --- @dep modules.control.jail
 
 local Roles = {
     _prototype={},
@@ -368,7 +369,15 @@ function Roles.assign_player(player, roles, by_player_name, skip_checks, silent)
     if not skip_checks and not valid_player then return end
     if not player then return end
     if type(roles) ~= 'table' or roles.name then
-        roles = {roles}
+        roles = { roles }
+    end
+    if Roles.player_has_role(player, "Jail") then
+        local to_assign = JailOldRole.old_roles[valid_player.name] or {}
+        for _, role in ipairs(roles) do
+            table.insert(to_assign, role)
+        end
+        JailOldRole.old_roles[valid_player.name] = to_assign
+        return
     end
     for _, role in ipairs(roles) do
         role = Roles.get_role_from_any(role)
diff --git a/modules/control/jail.lua b/modules/control/jail.lua
index 1e37fbfa..93a02734 100644
--- a/modules/control/jail.lua
+++ b/modules/control/jail.lua
@@ -19,6 +19,7 @@
 local Roles = require 'expcore.roles' --- @dep expcore.roles
 local Game = require 'utils.game' --- @dep utils.game
 local Global = require 'utils.global' --- @dep utils.global
+local JailOldRole = require 'modules.control.jail_old_role' --- @dep modules.control.jail_old_role
 
 local valid_player = Game.get_player_from_any
 local assign_roles = Roles.assign_player
@@ -89,7 +90,7 @@ function Jail.jail_player(player, by_player_name, reason)
 
     if has_role(player, 'Jail') then return end
     local roles = get_roles(player)
-    old_roles[player.name] = roles
+    JailOldRole.old_roles[player.name] = roles
 
     player.walking_state = { walking = false }
     player.riding_state = { acceleration = defines.riding.acceleration.nothing, direction = player.riding_state.direction }
@@ -116,14 +117,25 @@ function Jail.unjail_player(player, by_player_name)
     if not by_player_name then return end
 
     if not has_role(player, 'Jail') then return end
-    local roles = old_roles[player.name] or {}
+    local roles = JailOldRole.old_roles[player.name] or {}
 
-    assign_roles(player, roles, by_player_name, nil, true)
     unassign_roles(player, 'Jail', by_player_name, nil, true)
+    assign_roles(player, roles, by_player_name, nil, true)
 
     event_emit(Jail.events.on_player_unjailed, player, by_player_name)
 
     return true
 end
 
-return Jail
\ No newline at end of file
+function Jail.add_old_role(player, to_assign)
+    player = valid_player(player)
+    if not player then return end
+
+    if not has_role(player, 'Jail') then return end
+    local roles = JailOldRole.old_roles[player.name]
+    if not roles then return end
+
+    table.insert(roles, to_assign)
+end
+
+return Jail
diff --git a/modules/control/jail_old_role.lua b/modules/control/jail_old_role.lua
new file mode 100644
index 00000000..0bf5d836
--- /dev/null
+++ b/modules/control/jail_old_role.lua
@@ -0,0 +1,13 @@
+local Global = require 'utils.global' --- @dep utils.global
+
+local Jail = {
+    old_roles = {}
+}
+
+local old_roles = Jail.old_roles
+Global.register(old_roles, function(tbl)
+    Jail.old_roles = tbl
+    old_roles = tbl
+end)
+
+return Jail