diff --git a/AsuroTool/ApplicationData.h b/AsuroTool/ApplicationData.h
index 4d0b718..4a251d7 100644
--- a/AsuroTool/ApplicationData.h
+++ b/AsuroTool/ApplicationData.h
@@ -50,11 +50,20 @@ public:
 	std::unordered_map<std::string, std::vector<time_t>> tasks = {};
 };
 
+enum class HoverTargetType
+{
+	HOVER_TARGET_NONE = 0,
+	HOVER_TARGET_CHECKLIST_DAY = 1,
+};
+
 class ApplicationData {
 public:
 	ApplicationSettings settings = {};
 	size_t checklistLength = 0;
+	int checklistHighlightDurationDays = 3;
 	std::shared_ptr<AudioData> audioData = std::make_shared<AudioData>();
+	HoverTargetType hoverTargetType = HoverTargetType::HOVER_TARGET_NONE;
+	time_t hoverTargetDay = 0;
 
 	//ApplicationData(const ApplicationData&) = delete;
 	//ApplicationData& operator=(const ApplicationData&) = delete;
diff --git a/AsuroTool/AsuroTool.cpp b/AsuroTool/AsuroTool.cpp
index 11b6e19..2fd1831 100644
--- a/AsuroTool/AsuroTool.cpp
+++ b/AsuroTool/AsuroTool.cpp
@@ -83,7 +83,7 @@ void init(DrawData& drawData, ApplicationData& appData)
 	ImFontConfig icons_config;
 	icons_config.MergeMode = true;
 	icons_config.PixelSnapH = true;
-	icons_config.GlyphOffset = { 0., 2. };
+	icons_config.GlyphOffset = { 0., 1. };
 	std::string iconFontPath = std::string(appPathStr);
 	iconFontPath.append("\\remixicon.ttf");
 	io.Fonts->AddFontFromFileTTF(iconFontPath.c_str(), 14.0f, &icons_config, icons_ranges);
@@ -99,6 +99,7 @@ void init(DrawData& drawData, ApplicationData& appData)
 void draw(DrawData& drawData, ApplicationData& appData)
 {
 	justDocked = false;
+	appData.hoverTargetType = HoverTargetType::HOVER_TARGET_NONE;
 
 	if (isHidden)
 	{
@@ -140,6 +141,18 @@ void draw(DrawData& drawData, ApplicationData& appData)
 		glfwGetMonitorWorkarea(glfwGetPrimaryMonitor(), &monitorX, &monitorY, &monitorW, &monitorH);
 		glfwSetWindowPos(drawData.window, monitorX + monitorW - drawData.window_size.x, monitorY + monitorH - drawData.window_size.y);
 	}
+
+	if (appData.hoverTargetType == HoverTargetType::HOVER_TARGET_CHECKLIST_DAY)
+	{
+		tm time_tm;
+		localtime_s(&time_tm, &appData.hoverTargetDay);
+
+		ImGui::BeginTooltip();
+		char timeStr[32];
+		strftime(timeStr, 32, "%d.%m", &time_tm);
+		ImGui::Text(timeStr);
+		ImGui::EndTooltip();
+	}
 }
 
 void cleanup(DrawData& drawData, ApplicationData& appData)
@@ -266,6 +279,12 @@ void drawDayLineButton(ApplicationData& appData, ImDrawList* drawList, float lin
 		selectedDay = day;
 	}
 	ImGui::SetCursorScreenPos(pos);
+
+	if (ImGui::IsMouseHoveringRect(startPos, endPos, false))
+	{
+		appData.hoverTargetType = HoverTargetType::HOVER_TARGET_CHECKLIST_DAY;
+		appData.hoverTargetDay = day;
+	}
 }
 
 ImVec2 checklistWindow(ApplicationData& appData, const char* title)
@@ -308,6 +327,16 @@ ImVec2 checklistWindow(ApplicationData& appData, const char* title)
 			std::vector<time_t>& taskDates = appData.settings.tasks[taskName];
 			bool taskDone = std::any_of(taskDates.begin(), taskDates.end(), selectedDayMatcher);
 			
+			bool highlightButton = std::all_of(taskDates.begin(), taskDates.end(), [&](time_t t) {
+				double timeDiffSeconds = difftime(today, getDayStartOf(t));
+				return timeDiffSeconds >= appData.checklistHighlightDurationDays * 24 * 60 * 60 + 1;
+			});
+			if (highlightButton)
+			{
+				ImGui::PushStyleColor(ImGuiCol_FrameBg,        { .5f, .2f, .15f, 0.54f });
+				ImGui::PushStyleColor(ImGuiCol_FrameBgActive,  { .6f, .3f, .2f,  0.40f });
+				ImGui::PushStyleColor(ImGuiCol_FrameBgHovered, { .6f, .3f, .2f,  0.67f });
+			}
 			if (ImGui::Checkbox(taskName.c_str(), &taskDone))
 			{
 				if (taskDone)
@@ -319,8 +348,22 @@ ImVec2 checklistWindow(ApplicationData& appData, const char* title)
 					std::erase_if(taskDates, selectedDayMatcher);
 				}
 			}
+			if (highlightButton)
+			{
+				ImGui::PopStyleColor(3);
+			}
 			ImGui::SameLine();
 		}
+
+		if (ImGui::SmallButton(ICON_SETTINGS_FILL))
+		{
+			ImGui::OpenPopup("checklist settings");
+		}
+		if (ImGui::BeginPopup("checklist settings"))
+		{
+			ImGui::DragInt("Task highlight duration", &appData.checklistHighlightDurationDays, .05f, 1, 7, "%d days");
+			ImGui::EndPopup();
+		}
 	}
 
 	ImVec2 size = ImGui::GetWindowSize();