diff --git a/CMakeLists.txt b/CMakeLists.txt
index b4ef872eb6..57ebeefcfd 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -82,7 +82,7 @@ message(STATUS "Configuring OpenMW...")
 set(OPENMW_VERSION_MAJOR 0)
 set(OPENMW_VERSION_MINOR 50)
 set(OPENMW_VERSION_RELEASE 0)
-set(OPENMW_LUA_API_REVISION 86)
+set(OPENMW_LUA_API_REVISION 87)
 set(OPENMW_POSTPROCESSING_API_REVISION 3)
 
 set(OPENMW_VERSION_COMMITHASH "")
diff --git a/apps/openmw/mwbase/luamanager.hpp b/apps/openmw/mwbase/luamanager.hpp
index 61574de3ac..5772c555a3 100644
--- a/apps/openmw/mwbase/luamanager.hpp
+++ b/apps/openmw/mwbase/luamanager.hpp
@@ -75,6 +75,7 @@ namespace MWBase
             const MWRender::AnimPriority& priority, int blendMask, bool autodisable, float speedmult,
             std::string_view start, std::string_view stop, float startpoint, uint32_t loops, bool loopfallback)
             = 0;
+        virtual void jailTimeServed(const MWWorld::Ptr& actor, int days) = 0;
         virtual void skillLevelUp(const MWWorld::Ptr& actor, ESM::RefId skillId, std::string_view source) = 0;
         virtual void skillUse(const MWWorld::Ptr& actor, ESM::RefId skillId, int useType, float scale) = 0;
         virtual void onHit(const MWWorld::Ptr& attacker, const MWWorld::Ptr& victim, const MWWorld::Ptr& weapon,
diff --git a/apps/openmw/mwgui/jailscreen.cpp b/apps/openmw/mwgui/jailscreen.cpp
index 2fbaa8d8ac..9244e9dd2f 100644
--- a/apps/openmw/mwgui/jailscreen.cpp
+++ b/apps/openmw/mwgui/jailscreen.cpp
@@ -4,6 +4,7 @@
 #include <components/misc/strings/format.hpp>
 
 #include "../mwbase/environment.hpp"
+#include "../mwbase/luamanager.hpp"
 #include "../mwbase/mechanicsmanager.hpp"
 #include "../mwbase/windowmanager.hpp"
 #include "../mwbase/world.hpp"
@@ -86,46 +87,6 @@ namespace MWGui
 
         // We should not worsen corprus when in prison
         player.getClass().getCreatureStats(player).getActiveSpells().skipWorsenings(mDays * 24);
-
-        const auto& skillStore = MWBase::Environment::get().getESMStore()->get<ESM::Skill>();
-        std::set<const ESM::Skill*> skills;
-        for (int day = 0; day < mDays; ++day)
-        {
-            auto& prng = MWBase::Environment::get().getWorld()->getPrng();
-            const ESM::Skill* skill = skillStore.searchRandom({}, prng);
-            skills.insert(skill);
-
-            MWMechanics::SkillValue& value = player.getClass().getNpcStats(player).getSkill(skill->mId);
-            if (skill->mId == ESM::Skill::Security || skill->mId == ESM::Skill::Sneak)
-                value.setBase(std::min(100.f, value.getBase() + 1));
-            else
-                value.setBase(std::max(0.f, value.getBase() - 1));
-        }
-
-        const MWWorld::Store<ESM::GameSetting>& gmst
-            = MWBase::Environment::get().getESMStore()->get<ESM::GameSetting>();
-
-        std::string message;
-        if (mDays == 1)
-            message = gmst.find("sNotifyMessage42")->mValue.getString();
-        else
-            message = gmst.find("sNotifyMessage43")->mValue.getString();
-
-        message = Misc::StringUtils::format(message, mDays);
-
-        for (const ESM::Skill* skill : skills)
-        {
-            int skillValue = player.getClass().getNpcStats(player).getSkill(skill->mId).getBase();
-            std::string skillMsg = gmst.find("sNotifyMessage44")->mValue.getString();
-            if (skill->mId == ESM::Skill::Sneak || skill->mId == ESM::Skill::Security)
-                skillMsg = gmst.find("sNotifyMessage39")->mValue.getString();
-
-            skillMsg = Misc::StringUtils::format(skillMsg, skill->mName, skillValue);
-            message += "\n" + skillMsg;
-        }
-
-        std::vector<std::string> buttons;
-        buttons.emplace_back("#{Interface:OK}");
-        MWBase::Environment::get().getWindowManager()->interactiveMessageBox(message, buttons);
+        MWBase::Environment::get().getLuaManager()->jailTimeServed(player, mDays);
     }
 }
diff --git a/apps/openmw/mwlua/engineevents.cpp b/apps/openmw/mwlua/engineevents.cpp
index 6c652bccba..be7d249bfc 100644
--- a/apps/openmw/mwlua/engineevents.cpp
+++ b/apps/openmw/mwlua/engineevents.cpp
@@ -113,6 +113,15 @@ namespace MWLua
                 scripts->onSkillLevelUp(event.mSkill, event.mSource);
         }
 
+        void operator()(const OnJailTimeServed& event) const
+        {
+            MWWorld::Ptr actor = getPtr(event.mActor);
+            if (actor.isEmpty())
+                return;
+            if (auto* scripts = getLocalScripts(actor))
+                scripts->onJailTimeServed(event.mDays);
+        }
+
     private:
         MWWorld::Ptr getPtr(ESM::RefNum id) const
         {
diff --git a/apps/openmw/mwlua/engineevents.hpp b/apps/openmw/mwlua/engineevents.hpp
index fb9183eb7c..407739d60e 100644
--- a/apps/openmw/mwlua/engineevents.hpp
+++ b/apps/openmw/mwlua/engineevents.hpp
@@ -70,8 +70,13 @@ namespace MWLua
             std::string mSkill;
             std::string mSource;
         };
+        struct OnJailTimeServed
+        {
+            ESM::RefNum mActor;
+            int mDays;
+        };
         using Event = std::variant<OnActive, OnInactive, OnConsume, OnActivate, OnUseItem, OnNewExterior, OnTeleported,
-            OnAnimationTextKey, OnSkillUse, OnSkillLevelUp>;
+            OnAnimationTextKey, OnSkillUse, OnSkillLevelUp, OnJailTimeServed>;
 
         void clear() { mQueue.clear(); }
         void addToQueue(Event e) { mQueue.push_back(std::move(e)); }
diff --git a/apps/openmw/mwlua/localscripts.cpp b/apps/openmw/mwlua/localscripts.cpp
index d784328035..ad2913dd49 100644
--- a/apps/openmw/mwlua/localscripts.cpp
+++ b/apps/openmw/mwlua/localscripts.cpp
@@ -232,7 +232,7 @@ namespace MWLua
             [&](LuaUtil::LuaView& view) { addPackage("openmw.self", sol::make_object(view.sol(), &mData)); });
         registerEngineHandlers({ &mOnActiveHandlers, &mOnInactiveHandlers, &mOnConsumeHandlers, &mOnActivatedHandlers,
             &mOnTeleportedHandlers, &mOnAnimationTextKeyHandlers, &mOnPlayAnimationHandlers, &mOnSkillUse,
-            &mOnSkillLevelUp });
+            &mOnSkillLevelUp, &mOnJailTimeServed });
     }
 
     void LocalScripts::setActive(bool active, bool callHandlers)
diff --git a/apps/openmw/mwlua/localscripts.hpp b/apps/openmw/mwlua/localscripts.hpp
index b3ec647d0e..bc34576509 100644
--- a/apps/openmw/mwlua/localscripts.hpp
+++ b/apps/openmw/mwlua/localscripts.hpp
@@ -89,6 +89,7 @@ namespace MWLua
         {
             callEngineHandlers(mOnSkillLevelUp, skillId, source);
         }
+        void onJailTimeServed(int days) { callEngineHandlers(mOnJailTimeServed, days); }
 
         void applyStatsCache();
 
@@ -118,6 +119,7 @@ namespace MWLua
         EngineHandlerList mOnPlayAnimationHandlers{ "_onPlayAnimation" };
         EngineHandlerList mOnSkillUse{ "_onSkillUse" };
         EngineHandlerList mOnSkillLevelUp{ "_onSkillLevelUp" };
+        EngineHandlerList mOnJailTimeServed{ "_onJailTimeServed" };
     };
 
 }
diff --git a/apps/openmw/mwlua/luamanagerimp.cpp b/apps/openmw/mwlua/luamanagerimp.cpp
index df9c9cd50f..850dd87eed 100644
--- a/apps/openmw/mwlua/luamanagerimp.cpp
+++ b/apps/openmw/mwlua/luamanagerimp.cpp
@@ -490,6 +490,11 @@ namespace MWLua
             EngineEvents::OnSkillLevelUp{ getId(actor), skillId.serializeText(), std::string(source) });
     }
 
+    void LuaManager::jailTimeServed(const MWWorld::Ptr& actor, int days)
+    {
+        mEngineEvents.addToQueue(EngineEvents::OnJailTimeServed{ getId(actor), days });
+    }
+
     void LuaManager::onHit(const MWWorld::Ptr& attacker, const MWWorld::Ptr& victim, const MWWorld::Ptr& weapon,
         const MWWorld::Ptr& ammo, int attackType, float attackStrength, float damage, bool isHealth,
         const osg::Vec3f& hitPos, bool successful, MWMechanics::DamageSourceType sourceType)
diff --git a/apps/openmw/mwlua/luamanagerimp.hpp b/apps/openmw/mwlua/luamanagerimp.hpp
index f47b6f96cf..bd4ab0d30e 100644
--- a/apps/openmw/mwlua/luamanagerimp.hpp
+++ b/apps/openmw/mwlua/luamanagerimp.hpp
@@ -92,6 +92,7 @@ namespace MWLua
             bool loopfallback) override;
         void skillUse(const MWWorld::Ptr& actor, ESM::RefId skillId, int useType, float scale) override;
         void skillLevelUp(const MWWorld::Ptr& actor, ESM::RefId skillId, std::string_view source) override;
+        void jailTimeServed(const MWWorld::Ptr& actor, int days) override;
         void onHit(const MWWorld::Ptr& attacker, const MWWorld::Ptr& victim, const MWWorld::Ptr& weapon,
             const MWWorld::Ptr& ammo, int attackType, float attackStrength, float damage, bool isHealth,
             const osg::Vec3f& hitPos, bool successful, MWMechanics::DamageSourceType sourceType) override;
diff --git a/apps/openmw/mwlua/uibindings.cpp b/apps/openmw/mwlua/uibindings.cpp
index 826338ca7d..8d9892005c 100644
--- a/apps/openmw/mwlua/uibindings.cpp
+++ b/apps/openmw/mwlua/uibindings.cpp
@@ -108,6 +108,10 @@ namespace MWLua
                   }
                   luaManager->addUIMessage(message, mode);
               };
+
+        api["_showInteractiveMessage"] = [windowManager](std::string_view message, sol::optional<sol::table>) {
+            windowManager->interactiveMessageBox(message, { "#{Interface:OK}" });
+        };
         api["CONSOLE_COLOR"] = LuaUtil::makeStrictReadOnly(LuaUtil::tableFromPairs<std::string, Misc::Color>(lua,
             {
                 { "Default", Misc::Color::fromHex(MWBase::WindowManager::sConsoleColor_Default.substr(1)) },
diff --git a/files/data/scripts/omw/mechanics/playercontroller.lua b/files/data/scripts/omw/mechanics/playercontroller.lua
index 6de31afdea..a0d1b11362 100644
--- a/files/data/scripts/omw/mechanics/playercontroller.lua
+++ b/files/data/scripts/omw/mechanics/playercontroller.lua
@@ -39,7 +39,8 @@ end
 
 local function skillLevelUpHandler(skillid, source, params)
     local skillStat = NPC.stats.skills[skillid](self)
-    if skillStat.base >= 100 then 
+    if (skillStat.base >= 100 and params.skillIncreaseValue > 0) or 
+        (skillStat.base <= 0 and params.skillIncreaseValue < 0) then 
         return false 
     end
 
@@ -62,25 +63,67 @@ local function skillLevelUpHandler(skillid, source, params)
             = levelStat.skillIncreasesForSpecialization[params.levelUpSpecialization] + params.levelUpSpecializationIncreaseValue;
     end
 
-    local skillRecord = Skill.record(skillid)
-    local npcRecord = NPC.record(self)
-    local class = NPC.classes.record(npcRecord.class)
+    if source ~= 'jail' then
+        local skillRecord = Skill.record(skillid)
+        local npcRecord = NPC.record(self)
+        local class = NPC.classes.record(npcRecord.class)
 
-    ambient.playSound("skillraise")
+        ambient.playSound("skillraise")
 
-    local message = string.format(core.getGMST('sNotifyMessage39'),skillRecord.name,skillStat.base)
+        local message = string.format(core.getGMST('sNotifyMessage39'),skillRecord.name,skillStat.base)
 
-    if source == I.SkillProgression.SKILL_INCREASE_SOURCES.Book then
-        message = '#{sBookSkillMessage}\n'..message
+        if source == I.SkillProgression.SKILL_INCREASE_SOURCES.Book then
+            message = '#{sBookSkillMessage}\n'..message
+        end
+
+        ui.showMessage(message, { showInDialogue = false })
+        
+        if levelStat.progress >= core.getGMST('iLevelUpTotal') then
+            ui.showMessage('#{sLevelUpMsg}', { showInDialogue = false })
+        end
+        
+        if not source or source == I.SkillProgression.SKILL_INCREASE_SOURCES.Usage then skillStat.progress = 0 end
     end
+end
 
-    ui.showMessage(message, { showInDialogue = false })
+local function jailTimeServed(days)
+    if not days or days <= 0 then
+        return
+    end
     
-    if levelStat.progress >= core.getGMST('iLevelUpTotal') then
-        ui.showMessage('#{sLevelUpMsg}', { showInDialogue = false })
+    local oldSkillLevels = {}
+    local skillByNumber = {}
+    for skillid, skillStat in pairs(NPC.stats.skills) do
+        oldSkillLevels[skillid] = skillStat(self).base
+        skillByNumber[#skillByNumber+1] = skillid
+    end
+    
+    math.randomseed(core.getSimulationTime())
+    for day=1,days do
+        local skillid = skillByNumber[math.random(#skillByNumber)]
+        -- skillLevelUp() handles skill-based increase/decrease
+        I.SkillProgression.skillLevelUp(skillid, I.SkillProgression.SKILL_INCREASE_SOURCES.Jail)
     end
 
-    if not source or source == I.SkillProgression.SKILL_INCREASE_SOURCES.Usage then skillStat.progress = 0 end
+    local message = ''
+    if days == 1 then
+        message = string.format(core.getGMST('sNotifyMessage42'), days)
+    else
+        message = string.format(core.getGMST('sNotifyMessage43'), days)
+    end
+    for skillid, skillStat in pairs(NPC.stats.skills) do
+        local diff = skillStat(self).base - oldSkillLevels[skillid]
+        if diff ~= 0 then
+            local skillMsg = core.getGMST('sNotifyMessage39')
+            if diff < 0 then
+                skillMsg = core.getGMST('sNotifyMessage44')
+            end
+            local skillRecord = Skill.record(skillid)
+            message = message..'\n'..string.format(skillMsg, skillRecord.name, skillStat(self).base)
+        end
+    end
+    
+    I.UI.showInteractiveMessage(message)
 end
 
 local function skillUsedHandler(skillid, params)
@@ -114,6 +157,7 @@ I.SkillProgression.addSkillLevelUpHandler(skillLevelUpHandler)
 return {
     engineHandlers = {
         onUpdate = onUpdate,
+        _onJailTimeServed = jailTimeServed,
     },
 
     eventHandlers = {
diff --git a/files/data/scripts/omw/skillhandlers.lua b/files/data/scripts/omw/skillhandlers.lua
index d3a224dc46..9b58d81174 100644
--- a/files/data/scripts/omw/skillhandlers.lua
+++ b/files/data/scripts/omw/skillhandlers.lua
@@ -38,6 +38,7 @@ local Skill = core.stats.Skill
 -- Table of all existing sources for skill increases. Any sources not listed below will be treated as equal to Trainer.
 -- @type SkillLevelUpSource
 -- @field #string Book book
+-- @field #string Jail jail
 -- @field #string Trainer trainer
 -- @field #string Usage usage
 
@@ -131,15 +132,17 @@ local function skillLevelUp(skillid, source)
         levelUpAttributeIncreaseValue = core.getGMST('iLevelUpMajorMultAttribute')
     end
 
-    local options = 
-    {
-        skillIncreaseValue = 1,
-        levelUpProgress = levelUpProgress,
-        levelUpAttribute = skillRecord.attribute,
-        levelUpAttributeIncreaseValue = levelUpAttributeIncreaseValue,
-        levelUpSpecialization = skillRecord.specialization,
-        levelUpSpecializationIncreaseValue = core.getGMST('iLevelupSpecialization'),
-    }
+    local options = {}
+    if source == 'jail' and not (skillid == 'security' or skillid == 'sneak') then
+        options.skillIncreaseValue = -1
+    else
+        options.skillIncreaseValue = 1
+        options.levelUpProgress = levelUpProgress
+        options.levelUpAttribute = skillRecord.attribute
+        options.levelUpAttributeIncreaseValue = levelUpAttributeIncreaseValue
+        options.levelUpSpecialization = skillRecord.specialization
+        options.levelUpSpecializationIncreaseValue = core.getGMST('iLevelupSpecialization')
+    end
 
     for i = #skillLevelUpHandlers, 1, -1 do
         if skillLevelUpHandlers[i](skillid, source, options) == false then
@@ -156,8 +159,15 @@ return {
     -- @context local
     -- @usage local I = require('openmw.interfaces')
     --
+    -- -- Make jail time hurt sneak skill instead of benefitting it
+    -- I.SkillProgression.addSkillLevelUpHandler(function(skillid, source, options) 
+    --     if skillid == 'sneak' and source == 'jail' and options.skillIncreaseValue > 0 then
+    --          options.skillIncreaseValue = -options.skillIncreaseValue
+    --     end
+    -- end)
+    --
     -- -- Forbid increasing destruction skill past 50
-    -- I.SkillProgression.addSkillLevelUpHandler(function(skillid, options) 
+    -- I.SkillProgression.addSkillLevelUpHandler(function(skillid, source, options) 
     --     if skillid == 'destruction' and types.NPC.stats.skills.destruction(self).base >= 50 then
     --         return false
     --     end
@@ -187,7 +197,7 @@ return {
         -- a modifiable table of skill level up values, and can be modified to change the behavior of later handlers. 
         -- These values are calculated based on vanilla mechanics. Setting any value to nil will cause that mechanic to be skipped. By default contains these values:
         --
-        --   * `skillIncreaseValue` - The numeric amount of skill levels gained.
+        --   * `skillIncreaseValue` - The numeric amount of skill levels gained. By default this is 1, except when the source is jail in which case it will instead be -1 for all skills except sneak and security.
         --   * `levelUpProgress` - The numeric amount of level up progress gained.
         --   * `levelUpAttribute` - The string identifying the attribute that should receive points from this skill level up.
         --   * `levelUpAttributeIncreaseValue` - The numeric amount of attribute increase points received. This contributes to the amount of each attribute the character receives during a vanilla level up.
@@ -263,7 +273,7 @@ return {
         --- Trigger a skill level up, activating relevant handlers
         -- @function [parent=#SkillProgression] skillLevelUp
         -- @param #string skillid The id of the skill to level up.
-        -- @param #SkillLevelUpSource source The source of the skill increase.
+        -- @param #SkillLevelUpSource source The source of the skill increase. Note that passing a value of @{#SkillLevelUpSource.Jail} will cause a skill decrease for all skills except sneak and security.
         skillLevelUp = skillLevelUp,
         
         --- @{#SkillLevelUpSource}
@@ -272,6 +282,7 @@ return {
             Book = 'book',
             Usage = 'usage',
             Trainer = 'trainer',
+            Jail = 'jail',
         },
         
         --- Compute the total skill gain required to level up a skill based on its current level, and other modifying factors such as major skills and specialization.
diff --git a/files/data/scripts/omw/ui.lua b/files/data/scripts/omw/ui.lua
index 31502fd6ee..c63c085fab 100644
--- a/files/data/scripts/omw/ui.lua
+++ b/files/data/scripts/omw/ui.lua
@@ -171,7 +171,7 @@ return {
     interface = {
         --- Interface version
         -- @field [parent=#UI] #number version
-        version = 2,
+        version = 3,
 
         --- All available UI modes.
         -- Use `view(I.UI.MODE)` in `luap` console mode to see the list.
@@ -254,6 +254,13 @@ return {
         -- @return #boolean
         isWindowVisible = isWindowVisible,
 
+        ---
+        -- Shows a message as an interactive message box pausing the game, with a single button with the localized text OK.
+        -- @function [parent=#UI] showInteractiveMessage
+        -- @param #string message Message to display
+        -- @param #table options Options (none yet)
+        showInteractiveMessage = ui._showInteractiveMessage
+
         -- TODO
         -- registerHudElement = function(name, showFn, hideFn) end,
         -- showHudElement = function(name, bool) end,