diff --git a/module_logs.lua b/module_logs.lua
index 9e89697..b4146fc 100644
--- a/module_logs.lua
+++ b/module_logs.lua
@@ -2,258 +2,362 @@
 -- This file is part of the "Not a Bot" application
 -- For conditions of distribution and use, see copyright notice in LICENSE
 
-local client = Client
-local discordia = Discordia
-local bot = Bot
-local enums = discordia.enums
+local Bot = Bot
+local Client = Client
+local Discordia = Discordia
+local Clock = Discordia.Clock
+local Date = Discordia.Date
+
 
 Module.Name = "logs"
 
+local messagesToDelete = {}
+
 function Module:GetConfigTable()
 	return {
-        {
-            Name = "ChannelManagementLogChannel",
-            Description = "Where channel created/updated/deleted should be logged",
-            Type = bot.ConfigType.Channel,
-            Optional = true
-        },
+		{
+			Name = "ChannelManagementLogChannel",
+			Description = "Where channel created/updated/deleted should be logged",
+			Type = Bot.ConfigType.Channel,
+			Optional = true
+		},
 		{
 			Name = "DeletedMessageChannel",
 			Description = "Where deleted messages should be logged",
-			Type = bot.ConfigType.Channel,
+			Type = Bot.ConfigType.Channel,
+			Optional = true
+		},
+		{
+			Name = "EnableLogRotation",
+			Description = "Enable log rotation",
+			Type = Bot.ConfigType.Boolean,
+			Default = false
+		},
+		{
+			Name = "LogRetentionPeriod",
+			Description = "The retention period of logs",
+			Type = Bot.ConfigType.Duration,
+			Default = 2 * 365 * 24 * 60 * 60 -- 2 years
+		},
+		{
+			Name = "IgnoredDeletedMessageChannels",
+			Description = "Messages deleted in those channels will not be logged",
+			Type = Bot.ConfigType.Channel,
+			Array = true,
+			Default = {}
+		},
+		{
+			Name = "NicknameChangedLogChannel",
+			Description = "Where nickname changes should be logged",
+			Type = Bot.ConfigType.Channel,
 			Optional = true
 		},
-        {
-            Name = "NicknameChangedLogChannel",
-            Description = "Where nickname changes should be logged",
-            Type = bot.ConfigType.Channel,
-            Optional = true
-        },
-        {
-            Name = "IgnoredDeletedMessageChannels",
-            Description = "Messages deleted in those channels will not be logged",
-            Type = bot.ConfigType.Channel,
-            Array = true,
-            Default = {}
-        },
 		{
 			Global = true,
 			Name = "PersistentMessageCacheSize",
 			Description = "How many of the last messages of every text channel should stay in bot memory?",
-			Type = bot.ConfigType.Integer,
+			Type = Bot.ConfigType.Integer,
 			Default = 50
 		},
 	}
 end
 
+
+function Module:OnLoaded()
+	self.RotationClock = Clock()
+	self.RotationClock:on("day", function ()
+		self:ForEachGuild(function (guildId, config, data, persistentData)
+			local guild = Client:getGuild(guildId)
+			if (guild) then
+				local config = self:GetConfig(guild)
+				if not config.EnableLogRotation then
+					return
+				end
+
+				Module:RotateLogs(guild,
+					config.LogRetentionPeriod,
+					{
+						config.ChannelManagementLogChannel,
+						config.DeletedMessageChannel,
+						config.NicknameChangedLogChannel,
+					}
+				)
+			end
+		end)
+	end)
+
+	self.DeletionClock = Clock()
+	self.DeletionClock:on("sec", function ()
+		if next(messagesToDelete) then
+			table.remove(messagesToDelete):delete()
+		end
+	end)
+
+	return true
+end
+
+function Module:OnUnload()
+	self.RotationClock:stop()
+	self.DeletionClock:stop()
+end
+
+function Module:OnReady()
+	self.RotationClock:start()
+	self.DeletionClock:start()
+end
+
 function Module:OnEnable(guild)
-    local data = self:GetData(guild)
+	local data = self:GetData(guild)
 
-    -- Keep a reference to the last X messages of every text channel
-    local messageCacheSize = self.GlobalConfig.PersistentMessageCacheSize
-    data.cachedMessages = {}
+	-- Keep a reference to the last X messages of every text channel
+	local messageCacheSize = self.GlobalConfig.PersistentMessageCacheSize
+	data.cachedMessages = {}
 
-    data.nicknames = {}
-    for userId, user in pairs(guild.members) do
-        data.nicknames[userId] = user.nickname
-    end
-    data.usernames = {}
-    for userId, user in pairs(guild.members) do
-        data.usernames[userId] = user._user._username
-    end
+	data.nicknames = {}
+	for userId, user in pairs(guild.members) do
+		data.nicknames[userId] = user.nickname
+	end
+	data.usernames = {}
+	for userId, user in pairs(guild.members) do
+		data.usernames[userId] = user._user._username
+	end
 
 	coroutine.wrap(function ()
-        for _, channel in pairs(guild.textChannels) do
-            data.cachedMessages[channel.id] = Bot:FetchChannelMessages(channel, nil, messageCacheSize, true)
-        end
-    end)()
+		for _, channel in pairs(guild.textChannels) do
+			data.cachedMessages[channel.id] = Bot:FetchChannelMessages(channel, nil, messageCacheSize, true)
+		end
+	end)()
 
 	return true
 end
 
 function Module:OnChannelDelete(channel)
 	local guild = channel.guild
-    if not guild then
-        return
-    end
-
-    local data = self:GetData(guild)
-    data.cachedMessages[channel.id] = nil
-
-    local config = self:GetConfig(guild)
-    local channelManagementLogChannel = config.ChannelManagementLogChannel
-    if not channelManagementLogChannel then
-        return
-    end
-
-    local logChannel = guild:getChannel(channelManagementLogChannel)
-    if not logChannel then
-        self:LogWarning(guild, "Channel management log channel %s no longer exists", channelManagementLogChannel)
-        return
-    end
-
-    logChannel:send({
-        embed = {
-            title = "Channel deleted",
-            description = channel.name,
-            timestamp = discordia.Date():toISO('T', 'Z')
-        }
-    })
+	if not guild then
+		return
+	end
+
+	local data = self:GetData(guild)
+	data.cachedMessages[channel.id] = nil
+
+	local config = self:GetConfig(guild)
+	local channelManagementLogChannel = config.ChannelManagementLogChannel
+	if not channelManagementLogChannel then
+		return
+	end
+
+	local logChannel = guild:getChannel(channelManagementLogChannel)
+	if not logChannel then
+		self:LogWarning(guild, "Channel management log channel %s no longer exists", channelManagementLogChannel)
+		return
+	end
+
+	logChannel:send({
+		embed = {
+			title = "Channel deleted",
+			description = channel.name,
+			timestamp = Date():toISO('T', 'Z')
+		}
+	})
 end
 
 function Module:OnChannelCreate(channel)
-    local guild = channel.guild
-    if not guild then
-        return
-    end
-
-    local config = self:GetConfig(guild)
-    local channelManagementLogChannel = config.ChannelManagementLogChannel
-    if not channelManagementLogChannel then
-        return
-    end
-
-    local logChannel = guild:getChannel(channelManagementLogChannel)
-    if not logChannel then
-        self:LogWarning(guild, "Channel management log channel %s no longer exists", channelManagementLogChannel)
-        return
-    end
-
-    logChannel:send({
-        embed = {
-            title = "Channel created",
-            description = "<#" .. channel.id .. ">",
-            timestamp = discordia.Date():toISO('T', 'Z')
-        }
-    })
+	local guild = channel.guild
+	if not guild then
+		return
+	end
+
+	local config = self:GetConfig(guild)
+	local channelManagementLogChannel = config.ChannelManagementLogChannel
+	if not channelManagementLogChannel then
+		return
+	end
+
+	local logChannel = guild:getChannel(channelManagementLogChannel)
+	if not logChannel then
+		self:LogWarning(guild, "Channel management log channel %s no longer exists", channelManagementLogChannel)
+		return
+	end
+
+	logChannel:send({
+		embed = {
+			title = "Channel created",
+			description = "<#" .. channel.id .. ">",
+			timestamp = Date():toISO('T', 'Z')
+		}
+	})
 end
 
 function Module:OnMemberUpdate(member)
-    local guild = member.guild
-    if not guild then
-        return
-    end
+	local guild = member.guild
+	if not guild then
+		return
+	end
 
-    local config = self:GetConfig(guild)
-    local nicknameChangeLogChannel = config.NicknameChangedLogChannel
-    if not nicknameChangeLogChannel then
-        return
-    end
+	local config = self:GetConfig(guild)
+	local nicknameChangeLogChannel = config.NicknameChangedLogChannel
+	if not nicknameChangeLogChannel then
+		return
+	end
 
-    local logChannel = guild:getChannel(nicknameChangeLogChannel)
-    if not logChannel then
-        self:LogWarning(guild, "Channel management log channel %s no longer exists", nicknameChangeLogChannel)
-        return
-    end
+	local logChannel = guild:getChannel(nicknameChangeLogChannel)
+	if not logChannel then
+		self:LogWarning(guild, "Channel management log channel %s no longer exists", nicknameChangeLogChannel)
+		return
+	end
 
-    local data = self:GetData(guild)
+	local data = self:GetData(guild)
 
 	-- Ignore the first nickname change because new members tend to change it directly after joining which generates a lot of useless logs
-    if data.nicknames[member.id] ~= nil and data.nicknames[member.id] ~= member.name then
-        logChannel:send({
-            embed = {
-                title = "Nickname changed",
-                description = string.format("%s - `%s` → `%s`", member.mentionString, data.nicknames[member.id], member.name),
-                timestamp = discordia.Date():toISO('T', 'Z')
-            }
-        })
-    end
-
-    if data.usernames[member.id] ~= nil and data.usernames[member.id] ~= member.user.username then
-        logChannel:send({
-            embed = {
-                title = "Username changed",
-                description = string.format("%s - `%s` → `%s`", member.mentionString, data.usernames[member.id], member.user.username),
-                timestamp = discordia.Date():toISO('T', 'Z')
-            }
-        })
-    end
-
-    data.nicknames[member.id] = member.name
-    data.usernames[member.id] = member.user.username
+	if data.nicknames[member.id] ~= nil and data.nicknames[member.id] ~= member.name then
+		logChannel:send({
+			embed = {
+				title = "Nickname changed",
+				description = string.format("%s - `%s` → `%s`", member.mentionString, data.nicknames[member.id], member.name),
+				timestamp = Date():toISO('T', 'Z')
+			}
+		})
+	end
+
+	if data.usernames[member.id] ~= nil and data.usernames[member.id] ~= member.user.username then
+		logChannel:send({
+			embed = {
+				title = "Username changed",
+				description = string.format("%s - `%s` → `%s`", member.mentionString, data.usernames[member.id], member.user.username),
+				timestamp = Date():toISO('T', 'Z')
+			}
+		})
+	end
+
+	data.nicknames[member.id] = member.name
+	data.usernames[member.id] = member.user.username
 end
 
 function Module:OnMessageDelete(message)
-    local guild = message.guild
-    local config = self:GetConfig(guild)
+	local guild = message.guild
+	local config = self:GetConfig(guild)
 
-    if table.search(config.IgnoredDeletedMessageChannels, message.channel.id) then
-        return
-    end
+	if table.search(config.IgnoredDeletedMessageChannels, message.channel.id) then
+		return
+	end
 
-    local deletedMessageChannel = config.DeletedMessageChannel
-    if not deletedMessageChannel then
-        return
-    end
+	local deletedMessageChannel = config.DeletedMessageChannel
+	if not deletedMessageChannel then
+		return
+	end
 
-    local logChannel = guild:getChannel(deletedMessageChannel)
-    if not logChannel then
-        self:LogWarning(guild, "Deleted message log channel %s no longer exists", deletedMessageChannel)
-        return
-    end
+	local logChannel = guild:getChannel(deletedMessageChannel)
+	if not logChannel then
+		self:LogWarning(guild, "Deleted message log channel %s no longer exists", deletedMessageChannel)
+		return
+	end
 
-    local desc = "🗑️ **Deleted message - sent by " .. message.author.mentionString .. " in " .. message.channel.mentionString .. "**\n"
+	local desc = "🗑️ **Deleted message - sent by " .. message.author.mentionString .. " in " .. message.channel.mentionString .. "**\n"
 
 	local embed = Bot:BuildQuoteEmbed(message, { initialContentSize = #desc })
-    embed.description = desc .. (embed.description or "")
+	embed.description = desc .. (embed.description or "")
 	embed.footer = {
 		text = string.format("Author ID: %s | Message ID: %s", message.author.id, message.id)
 	}
-    embed.timestamp = discordia.Date():toISO('T', 'Z')
+	embed.timestamp = Date():toISO('T', 'Z')
 
 	logChannel:send({
-        embed = embed
+		embed = embed
 	})
 end
 
 function Module:OnMessageDeleteUncached(channel, messageId)
-    local guild = channel.guild
-    local config = self:GetConfig(guild)
+	local guild = channel.guild
+	local config = self:GetConfig(guild)
 
-    if table.search(config.IgnoredDeletedMessageChannels, channel.id) then
-        return
-    end
+	if table.search(config.IgnoredDeletedMessageChannels, channel.id) then
+		return
+	end
 
-    local deletedMessageChannel = config.DeletedMessageChannel
-    if not deletedMessageChannel then
-        return
-    end
+	local deletedMessageChannel = config.DeletedMessageChannel
+	if not deletedMessageChannel then
+		return
+	end
 
-    local logChannel = guild:getChannel(deletedMessageChannel)
-    if not logChannel then
-        self:LogWarning(guild, "Deleted message log channel %s no longer exists", deletedMessageChannel)
-        return
-    end
+	local logChannel = guild:getChannel(deletedMessageChannel)
+	if not logChannel then
+		self:LogWarning(guild, "Deleted message log channel %s no longer exists", deletedMessageChannel)
+		return
+	end
 
 	logChannel:send({
-        embed = {
-            description = "🗑️ **Deleted message (uncached) - sent by <unknown> in " .. channel.mentionString .. "**",
-            footer = {
-                text = string.format("Message ID: %s", messageId)
-            },
-            timestamp = discordia.Date():toISO('T', 'Z')
-        }
+		embed = {
+			description = "🗑️ **Deleted message (uncached) - sent by <unknown> in " .. channel.mentionString .. "**",
+			footer = {
+				text = string.format("Message ID: %s", messageId)
+			},
+			timestamp = Date():toISO('T', 'Z')
+		}
 	})
 end
 
 function Module:OnMessageCreate(message)
 	local guild = message.guild
-    if not guild then
-        return
-    end
-
-    local data = self:GetData(guild)
-    local cachedMessages = data.cachedMessages[message.channel.id]
-    if not cachedMessages then
-        cachedMessages = {}
-        data.cachedMessages[message.channel.id] = cachedMessages
-    end
-
-    -- Remove oldest message from permanent cache and add the new message
-    table.insert(cachedMessages, message)
-
-    local messageCacheSize = self.GlobalConfig.PersistentMessageCacheSize
-    while #cachedMessages > messageCacheSize do
-        table.remove(cachedMessages, 1)
-    end
+	if not guild then
+		return
+	end
+
+	local data = self:GetData(guild)
+	local cachedMessages = data.cachedMessages[message.channel.id]
+	if not cachedMessages then
+		cachedMessages = {}
+		data.cachedMessages[message.channel.id] = cachedMessages
+	end
+
+	-- Remove oldest message from permanent cache and add the new message
+	table.insert(cachedMessages, message)
+
+	local messageCacheSize = self.GlobalConfig.PersistentMessageCacheSize
+	while #cachedMessages > messageCacheSize do
+		table.remove(cachedMessages, 1)
+	end
+end
+
+local function isMessageTooOld(message, logRetentionPeriod)
+	local messageTimestamp = Date.fromSnowflake(message.id):toSeconds()
+	return os.difftime(os.time(), messageTimestamp) > logRetentionPeriod
+end
+
+local function scheduleOldMessagesToDeletion(firstMessage, channel, logRetentionPeriod)
+	local buf = {}
+
+	repeat
+		-- Sort by id to keep the temporal order
+		local messages = channel:getMessagesAfter(firstMessage.id, 100):toArray("id")
+		table.insert(messages, 1, firstMessage)
+
+		for _, msg in ipairs(messages) do
+			if msg.author.id == Client.user.id
+			and (msg.embed and msg.embed.description and msg.embed.description:match("Deleted message"))
+			and isMessageTooOld(msg, logRetentionPeriod) then
+				table.insert(buf, msg)
+			end
+		end
+
+		firstMessage = messages[#messages]
+	until next(buf) or messages == nil
+
+	messagesToDelete = buf
+end
+
+function Module:RotateLogs(guild, logRetentionPeriod, logChannels)
+	local done = {}
+	for _, logChannelId in pairs(logChannels) do
+		if not done[logChannelId] then
+			local logChannel = guild:getChannel(logChannelId)
+			local firstMessage = logChannel:getFirstMessage()
+
+			if firstMessage then
+				scheduleOldMessagesToDeletion(firstMessage, logChannel, logRetentionPeriod)
+			end
+
+			done[logChannelId] = true
+		end
+	end
 end
+