diff --git a/pdf_viewer/config.cpp b/pdf_viewer/config.cpp
index 9c7ef4854..c9bbf23ab 100644
--- a/pdf_viewer/config.cpp
+++ b/pdf_viewer/config.cpp
@@ -80,7 +80,7 @@ extern bool FORCE_CUSTOM_LINE_ALGORITHM;
 extern float OVERVIEW_SIZE[2];
 extern float OVERVIEW_OFFSET[2];
 extern bool IGNORE_WHITESPACE_IN_PRESENTATION_MODE;
-extern bool EXACT_HIGHLIGHT_SELECT;
+extern bool LEGACY_WORD_SELECT;
 extern bool SHOW_DOC_PATH;
 extern float FASTREAD_OPACITY;
 extern bool SHOULD_WARN_ABOUT_USER_KEY_OVERRIDE;
@@ -397,7 +397,7 @@ ConfigManager::ConfigManager(const Path& default_path, const Path& auto_path ,co
 	configs.push_back({ L"overview_size", &OVERVIEW_SIZE, fvec2_serializer, fvec2_deserializer, nullptr });
 	configs.push_back({ L"overview_offset", &OVERVIEW_OFFSET, fvec2_serializer, fvec2_deserializer, nullptr });
 	configs.push_back({ L"ignore_whitespace_in_presentation_mode", &IGNORE_WHITESPACE_IN_PRESENTATION_MODE, bool_serializer, bool_deserializer, bool_validator });
-	configs.push_back({ L"exact_highlight_select", &EXACT_HIGHLIGHT_SELECT, bool_serializer, bool_deserializer, bool_validator });
+	configs.push_back({ L"legacy_word_select", &LEGACY_WORD_SELECT, bool_serializer, bool_deserializer, bool_validator });
 	configs.push_back({ L"show_doc_path", &SHOW_DOC_PATH, bool_serializer, bool_deserializer, bool_validator });
 	configs.push_back({ L"fastread_opacity", &FASTREAD_OPACITY, float_serializer, float_deserializer, nullptr });
 	configs.push_back({ L"should_warn_about_user_key_override", &SHOULD_WARN_ABOUT_USER_KEY_OVERRIDE, bool_serializer, bool_deserializer, bool_validator });
diff --git a/pdf_viewer/document.cpp b/pdf_viewer/document.cpp
index 6e6182015..a4375728c 100644
--- a/pdf_viewer/document.cpp
+++ b/pdf_viewer/document.cpp
@@ -26,6 +26,7 @@ extern bool CREATE_TABLE_OF_CONTENTS_IF_NOT_EXISTS;
 extern int MAX_CREATED_TABLE_OF_CONTENTS_SIZE;
 extern bool FORCE_CUSTOM_LINE_ALGORITHM;
 extern bool SUPER_FAST_SEARCH;
+extern bool LEGACY_WORD_SELECT;
 
 
 int Document::get_mark_index(char symbol) {
@@ -80,7 +81,7 @@ void Document::fill_highlight_rects(fz_context* ctx, fz_document* doc_) {
 		std::vector<fz_rect> highlight_rects;
 		std::vector<fz_rect> merged_rects;
 		std::wstring highlight_text;
-		get_text_selection(ctx, highlight.selection_begin, highlight.selection_end, true, highlight_rects, highlight_text, doc_);
+		get_text_selection(ctx, highlight.selection_begin, highlight.selection_end, LEGACY_WORD_SELECT, highlight_rects, highlight_text, doc_);
 		merge_selected_character_rects(highlight_rects, merged_rects);
 
 		if (i < highlights.size()) {
@@ -1533,7 +1534,7 @@ void Document::embed_annotations(std::wstring new_file_path) {
 		std::vector<fz_rect> selected_characters_page_rects;
 		std::wstring selected_text;
 
-		get_text_selection(highlight.selection_begin, highlight.selection_end, true, selected_characters, selected_text);
+		get_text_selection(highlight.selection_begin, highlight.selection_end, LEGACY_WORD_SELECT, selected_characters, selected_text);
 		merge_selected_character_rects(selected_characters, merged_characters);
 
 		for (auto absrect : merged_characters) {
diff --git a/pdf_viewer/document_view.cpp b/pdf_viewer/document_view.cpp
index afcb173b6..03c3f05ce 100644
--- a/pdf_viewer/document_view.cpp
+++ b/pdf_viewer/document_view.cpp
@@ -5,7 +5,6 @@ extern float MOVE_SCREEN_PERCENTAGE;
 extern float FIT_TO_PAGE_WIDTH_RATIO;
 extern float RULER_PADDING;
 extern float RULER_X_PADDING;
-extern bool EXACT_HIGHLIGHT_SELECT;
 extern bool IGNORE_STATUSBAR_IN_PRESENTATION_MODE;
 
 
@@ -199,6 +198,21 @@ void DocumentView::delete_closest_bookmark_to_offset(float offset) {
 	current_document->delete_closest_bookmark(offset);
 }
 
+void DocumentView::expand_highlight_with_index(int index) {
+	Highlight hl = get_highlight_with_index(index);
+	delete_highlight_with_index(index);
+	add_highlight(hl.selection_begin, hl.selection_end, true, hl.type);
+}
+
+void DocumentView::expand_all_highlights() {
+	std::size_t num_highlights = current_document->get_highlights().size();
+	if (num_highlights > 0) {
+		for (; num_highlights--;) {
+			expand_highlight_with_index(0);
+		}
+	}
+}
+
 float DocumentView::get_offset_x() {
 	return offset_x;
 }
@@ -298,17 +312,19 @@ void DocumentView::add_bookmark(std::wstring desc) {
 	}
 }
 
-void DocumentView::add_highlight(AbsoluteDocumentPos selection_begin, AbsoluteDocumentPos selection_end, char type) {
+void DocumentView::add_highlight(AbsoluteDocumentPos selection_begin, AbsoluteDocumentPos selection_end, bool is_word_selection, char type) {
 
 	if (current_document) {
 		std::vector<fz_rect> selected_characters;
 		std::vector<fz_rect> merged_characters;
 		std::wstring selected_text;
 
-		get_text_selection(selection_begin, selection_end, !EXACT_HIGHLIGHT_SELECT, selected_characters, selected_text);
+		get_text_selection(selection_begin, selection_end, is_word_selection, selected_characters, selected_text);
 		merge_selected_character_rects(selected_characters, merged_characters);
 		if (selected_text.size() > 0) {
-			current_document->add_highlight(selected_text, merged_characters, selection_begin, selection_end, type);
+			const fz_point center_begin = rect_get_center(selected_characters.front());
+			const fz_point center_end = rect_get_center(selected_characters.back());
+			current_document->add_highlight(selected_text, merged_characters, { center_begin.x, center_begin.y }, { center_end.x, center_end.y }, type);
 		}
 	}
 }
diff --git a/pdf_viewer/document_view.h b/pdf_viewer/document_view.h
index ffe1c7701..f62783d76 100644
--- a/pdf_viewer/document_view.h
+++ b/pdf_viewer/document_view.h
@@ -78,6 +78,8 @@ class DocumentView {
 	void delete_highlight_with_index(int index);
 	void delete_highlight(Highlight hl);
 	void delete_closest_bookmark_to_offset(float offset);
+	void expand_highlight_with_index(int index);
+	void expand_all_highlights();
 	float get_offset_x();
 	float get_offset_y();
 	AbsoluteDocumentPos get_offsets();
@@ -91,7 +93,7 @@ class DocumentView {
 	void get_text_selection(AbsoluteDocumentPos selection_begin, AbsoluteDocumentPos selection_end, bool is_word_selection, std::vector<fz_rect>& selected_characters, std::wstring& text_selection);
 	void add_mark(char symbol);
 	void add_bookmark(std::wstring desc);
-	void add_highlight(AbsoluteDocumentPos selection_begin, AbsoluteDocumentPos selection_end, char type);
+	void add_highlight(AbsoluteDocumentPos selection_begin, AbsoluteDocumentPos selection_end, bool is_word_selection, char type);
 	void on_view_size_change(int new_width, int new_height);
 	void absolute_to_window_pos(float absolute_x, float absolute_y, float* window_x, float* window_y);
 	//void absolute_to_window_pos_pixels(float absolute_x, float absolute_y, float* window_x, float* window_y);
diff --git a/pdf_viewer/input.cpp b/pdf_viewer/input.cpp
index faaac2db1..28b91cb6c 100644
--- a/pdf_viewer/input.cpp
+++ b/pdf_viewer/input.cpp
@@ -628,6 +628,30 @@ class DeleteHighlightCommand : public Command {
 	}
 };
 
+class ExpandHighlightCommand : public Command {
+	void perform(MainWidget* widget) {
+		if (widget->selected_highlight_index != -1) {
+			widget->main_document_view->expand_highlight_with_index(widget->selected_highlight_index);
+		}
+		widget->validate_render();
+	}
+
+	std::string get_name() {
+		return "expand_highlight";
+	}
+};
+
+class ExpandAllHighlightsCommand : public Command {
+	void perform(MainWidget* widget) {
+		widget->main_document_view->expand_all_highlights();
+		widget->validate_render();
+	}
+
+	std::string get_name() {
+		return "expand_all_highlights";
+	}
+};
+
 class GotoPortalCommand : public Command {
 	void perform(MainWidget* widget) {
 		std::optional<Portal> link = widget->main_document_view->find_closest_portal();
@@ -1530,7 +1554,7 @@ class SetSelectHighlightTypeCommand : public SymbolCommand {
 class AddHighlightWithCurrentTypeCommand : public Command {
 	void perform(MainWidget* widget) {
         if (widget->main_document_view->selected_character_rects.size() > 0) {
-            widget->main_document_view->add_highlight(widget->selection_begin, widget->selection_end, widget->select_highlight_type);
+            widget->main_document_view->add_highlight(widget->selection_begin, widget->selection_end, widget->is_word_selection, widget->select_highlight_type);
             widget->main_document_view->selected_character_rects.clear();
             widget->selected_text.clear();
         }
@@ -2225,6 +2249,8 @@ CommandManager::CommandManager(ConfigManager* config_manager) {
 	new_commands["delete_portal"] = []() {return std::make_unique< DeletePortalCommand>(); };
 	new_commands["delete_bookmark"] = []() {return std::make_unique< DeleteBookmarkCommand>(); };
 	new_commands["delete_highlight"] = []() {return std::make_unique< DeleteHighlightCommand>(); };
+	new_commands["expand_highlight"] = []() {return std::make_unique< ExpandHighlightCommand>(); };
+	new_commands["expand_all_highlights"] = []() {return std::make_unique< ExpandAllHighlightsCommand>(); };
 	new_commands["goto_link"] = []() {return std::make_unique< GotoPortalCommand>(); };
 	new_commands["goto_portal"] = []() {return std::make_unique< GotoPortalCommand>(); };
 	new_commands["edit_link"] = []() {return std::make_unique< EditPortalCommand>(); };
diff --git a/pdf_viewer/keys.config b/pdf_viewer/keys.config
index 700767d4e..f0b97d816 100644
--- a/pdf_viewer/keys.config
+++ b/pdf_viewer/keys.config
@@ -184,6 +184,8 @@ goto_highlight gh
 goto_highlight_g gH
 # Left click on a highlight and then press the `delete_highlight` shortcut to delete it.
 delete_highlight dh
+# Left click on a highlight and then press the `expand_highlight` shortcut to expand it to its word boundaries
+expand_highlight eh
 
 # Sets the highlight type to be used for other operations (the default highlight type is 'a')
 #set_select_highlight_type
diff --git a/pdf_viewer/main.cpp b/pdf_viewer/main.cpp
index 61c4f4592..30ec6eca3 100644
--- a/pdf_viewer/main.cpp
+++ b/pdf_viewer/main.cpp
@@ -198,7 +198,6 @@ bool FORCE_CUSTOM_LINE_ALGORITHM = false;
 float OVERVIEW_SIZE[2] = { 0.8f, 0.4f };
 float OVERVIEW_OFFSET[2] = { 0.0f, 0.0f };
 bool IGNORE_WHITESPACE_IN_PRESENTATION_MODE = false;
-bool EXACT_HIGHLIGHT_SELECT = false;
 bool SHOW_DOC_PATH = false;
 float FASTREAD_OPACITY = 0.5f;
 bool SHOULD_WARN_ABOUT_USER_KEY_OVERRIDE = true;
@@ -215,6 +214,7 @@ float HYPERDRIVE_SPEED_FACTOR = 10.0f;
 float SMOOTH_SCROLL_SPEED = 3.0f;
 float SMOOTH_SCROLL_DRAG = 3000.0f;
 int PRERENDERED_PAGE_COUNT = 0;
+bool LEGACY_WORD_SELECT = false;
 
 float PAGE_SEPARATOR_WIDTH = 0.0f;
 float PAGE_SEPARATOR_COLOR[3] = {0.9f, 0.9f, 0.9f};
diff --git a/pdf_viewer/main_widget.cpp b/pdf_viewer/main_widget.cpp
index c22e31bc6..65ded5927 100644
--- a/pdf_viewer/main_widget.cpp
+++ b/pdf_viewer/main_widget.cpp
@@ -296,7 +296,7 @@ void MainWidget::mouseMoveEvent(QMouseEvent* mouse_event) {
 
             main_document_view->get_text_selection(selection_begin,
                 selection_end,
-                is_word_selecting,
+                is_word_selection,
                 main_document_view->selected_character_rects,
                 selected_text);
 
@@ -1409,7 +1409,7 @@ void MainWidget::handle_left_click(WindowPos click_pos, bool down, bool is_shift
         if (!mouse_drag_mode) {
             is_selecting = true;
 			if (SINGLE_CLICK_SELECTS_WORDS) {
-				is_word_selecting = true;
+				is_word_selection = true;
 			}
         }
         else {
@@ -1438,10 +1438,9 @@ void MainWidget::handle_left_click(WindowPos click_pos, bool down, bool is_shift
 
             main_document_view->get_text_selection(last_mouse_down,
                 abs_doc_pos,
-                is_word_selecting,
+                is_word_selection,
                 main_document_view->selected_character_rects,
                 selected_text);
-            is_word_selecting = false;
         }
         else {
             handle_click(click_pos);
@@ -1657,7 +1656,7 @@ void MainWidget::mouseReleaseEvent(QMouseEvent* mevent) {
         else {
 			handle_left_click({ mevent->pos().x(), mevent->pos().y() }, false, is_shift_pressed, is_control_pressed, is_alt_pressed);
 			if (is_select_highlight_mode && (main_document_view->selected_character_rects.size() > 0)) {
-				main_document_view->add_highlight(selection_begin, selection_end, select_highlight_type);
+				main_document_view->add_highlight(selection_begin, selection_end, is_word_selection, select_highlight_type);
                 clear_selected_text();
 			}
 			if (main_document_view->selected_character_rects.size() > 0) {
@@ -1703,10 +1702,10 @@ void MainWidget::mouseDoubleClickEvent(QMouseEvent* mevent) {
 	if (mevent->button() == Qt::MouseButton::LeftButton) {
 		is_selecting = true;
 		if (SINGLE_CLICK_SELECTS_WORDS) {
-			is_word_selecting = false;
+			is_word_selection = false;
 		}
         else {
-			is_word_selecting = true;
+			is_word_selection = true;
 		}
 	}
 }
@@ -3678,14 +3677,14 @@ void MainWidget::handle_goto_bookmark_global() {
 
 void MainWidget::handle_add_highlight(char symbol) {
 	if (main_document_view->selected_character_rects.size() > 0) {
-		main_document_view->add_highlight(selection_begin, selection_end, symbol);
+		main_document_view->add_highlight(selection_begin, selection_end, is_word_selection, symbol);
 		main_document_view->selected_character_rects.clear();
 		selected_text.clear();
 	}
 	else if (selected_highlight_index != -1) {
 		Highlight new_highlight = main_document_view->get_highlight_with_index(selected_highlight_index);
 		main_document_view->delete_highlight_with_index(selected_highlight_index);
-		main_document_view->add_highlight(new_highlight.selection_begin, new_highlight.selection_end, symbol);
+		main_document_view->add_highlight(new_highlight.selection_begin, new_highlight.selection_end, is_word_selection, symbol);
 		selected_highlight_index = -1;
 	}
 }
diff --git a/pdf_viewer/main_widget.h b/pdf_viewer/main_widget.h
index b4b0adff9..51bc65f9e 100644
--- a/pdf_viewer/main_widget.h
+++ b/pdf_viewer/main_widget.h
@@ -88,7 +88,7 @@ class MainWidget : public QWidget, ConfigFileChangeListener{
 	// is the user currently selecing text? (happens when we left click and move the cursor)
 	bool is_selecting = false;
 	// is the user in word select mode? (happens when we double left click and move the cursor)
-	bool is_word_selecting = false;
+	bool is_word_selection = false;
 	std::wstring selected_text;
 
 	bool is_select_highlight_mode = false;
diff --git a/pdf_viewer/prefs.config b/pdf_viewer/prefs.config
index 4bbfc0be3..30c41385a 100644
--- a/pdf_viewer/prefs.config
+++ b/pdf_viewer/prefs.config
@@ -3,6 +3,9 @@
 # (can be 0 or 1) if set, shows a notification on startup if a new version of sioyek is available
 check_for_updates_on_startup	0
 
+# Force word selection mode for highlights read from database or when embedding into PDF files
+legacy_word_select 0
+
 # Use old keybind parsing method (only for backwards compatibility)
 use_legacy_keybinds 0
 
diff --git a/pdf_viewer/utils.cpp b/pdf_viewer/utils.cpp
index c53b3e404..f02dfdc1a 100644
--- a/pdf_viewer/utils.cpp
+++ b/pdf_viewer/utils.cpp
@@ -154,6 +154,10 @@ void rect_to_quad(fz_rect rect, float quad[8]) {
 	quad[7] = rect.y1;
 }
 
+fz_point rect_get_center(const fz_rect& rect) {
+	return { (rect.x0 + rect.x1) / 2, (rect.y0 + rect.y1) / 2 };
+}
+
 void copy_to_clipboard(const std::wstring& text, bool selection) {
 	auto clipboard = QGuiApplication::clipboard();
 	auto qtext = QString::fromStdWString(text);
@@ -600,7 +604,8 @@ fz_stext_char* find_closest_char_to_document_point(const std::vector<fz_stext_ch
 	int index = 0;
 	for (auto current_char : flat_chars) {
 
-		fz_point quad_center = current_char->origin;
+		// This works better than current_char->origin
+		const fz_point quad_center = rect_get_center(fz_rect_from_quad(current_char->quad));
 		float distance = dist_squared(document_point, quad_center);
 		if (distance < min_distance) {
 			min_distance = distance;
diff --git a/pdf_viewer/utils.h b/pdf_viewer/utils.h
index 10873c6c4..ed3a9c9f9 100644
--- a/pdf_viewer/utils.h
+++ b/pdf_viewer/utils.h
@@ -73,6 +73,7 @@ int argminf(const std::vector<T> &collection, std::function<float(T)> f) {
 	return min_index;
 }
 void rect_to_quad(fz_rect rect, float quad[8]);
+fz_point rect_get_center(const fz_rect& rect);
 void copy_to_clipboard(const std::wstring& text, bool selection=false);
 void install_app(const char* argv0);
 int get_f_key(std::wstring name);
diff --git a/resources/sioyek.1 b/resources/sioyek.1
index 1ad3a2d1e..ec25d1334 100644
--- a/resources/sioyek.1
+++ b/resources/sioyek.1
@@ -1263,12 +1263,6 @@ Offset of the overview window as floats from the center of the page.
 
 Always use fit_to_page_smart (ignoring whitespace) in presentation view.
 .HP
-.B exact_highlight_select
-.I boolean
-
-If set to 0, then in word select mode, select the whole word even if
-the cursor is only partially on the word. If set to 1, then select the word only if the range of the cursor's selection fully includes the word.
-.HP
 .B show_doc_path
 .I boolean
 
@@ -1312,6 +1306,12 @@ always attempted.
 If set to 0, search is performed by the mupdf backend. If set to 1, a super
 fast search index is used instead. This leads to a slight increase in memory.
 .HP
+.B legacy_word_select
+.I boolean
+
+If set to 1, highlights are expanded to entail entire words when read from the
+database or when embedded into PDF files.
+.HP
 .B case_sensitive_search
 .I boolean