diff --git a/gtk2_ardour/ardour_ui2.cc b/gtk2_ardour/ardour_ui2.cc
index 7d528abefc..88ed561517 100644
--- a/gtk2_ardour/ardour_ui2.cc
+++ b/gtk2_ardour/ardour_ui2.cc
@@ -91,7 +91,7 @@ ARDOUR_UI::setup_tooltips ()
 	ArdourCanvas::Canvas::set_tooltip_timeout (Gtk::Settings::get_default()->property_gtk_tooltip_timeout ());
 
 	set_tip (auto_return_button, _("Return to last playback start when stopped"));
-	set_tip (layered_button, _("When active, new recordings will be added as regions on a layer atop existing regions.\nWhen disabled, the underlying region will be spliced and replaced with the newly recorded region."));
+	set_tip (layered_button, _("<b>When active</b>, new recordings will be added as regions on a layer atop existing regions.\n<b>When disabled</b>, the underlying region will be spliced and replaced with the newly recorded region."));
 	set_tip (follow_edits_button, _("Playhead follows Range tool clicks, and Range selections"));
 	parameter_changed("click-gain");
 	set_tip (solo_alert_button, _("When active, something is soloed.\nClick to de-solo everything"));
@@ -101,8 +101,8 @@ ARDOUR_UI::setup_tooltips ()
 	set_tip (secondary_clock, _("<b>Secondary Clock</b> right-click to set display mode. Click to edit, click+drag a digit or mouse-over+scroll wheel to modify.\nText edits: right-to-left overwrite <tt>Esc</tt>: cancel; <tt>Enter</tt>: confirm; postfix the edit with '+' or '-' to enter delta times.\n"));
 	set_tip (editor_meter_peak_display, _("Reset All Peak Meters"));
 	set_tip (error_alert_button, _("Show Error Log and acknowledge warnings"));
-	set_tip (_cue_rec_enable, _("When enabled, triggering Cues will result in Cue Markers added to the timeline"));
-	set_tip (_cue_play_enable, _("When enabled, Cue Markers will trigger the associated Cue when passed on the timeline"));
+	set_tip (_cue_rec_enable, _("<b>When enabled</b>, triggering Cues will result in Cue Markers added to the timeline"));
+	set_tip (_cue_play_enable, _("<b>When enabled</b>, Cue Markers will trigger the associated Cue when passed on the timeline"));
 
 	set_tip (latency_disable_button, _("Disable all Plugin Delay Compensation. This results in the shortest delay from live input to output, but any paths with delay-causing plugins will sound later than those without."));
 
diff --git a/gtk2_ardour/ardour_ui_session.cc b/gtk2_ardour/ardour_ui_session.cc
index 18775d7ce3..67f3502c17 100644
--- a/gtk2_ardour/ardour_ui_session.cc
+++ b/gtk2_ardour/ardour_ui_session.cc
@@ -714,7 +714,7 @@ ARDOUR_UI::build_session_stage_two (std::string const& path, std::string const&
 		}
 
 		ArdourMessageDialog msg (string_compose(
-		                           _("Could not create session in \"%1\":.\nGlib Error\nDomain: %2\nCode: %3\nWhat: %4\n%5%6"),
+		                           _("Could not create session in \"%1\".\n\nGlib Error\nDomain: %2\nCode: %3\nWhat: %4\n%5%6"),
 		                           path,
 		                           g_quark_to_string(e.domain()), e.code(), glib_what.c_str(),
 		                           ss.str().empty() ? "" : "\n\n---", escaped_error_txt));
diff --git a/gtk2_ardour/audio_trigger_properties_box.cc b/gtk2_ardour/audio_trigger_properties_box.cc
index c271c843b2..99275e57ba 100644
--- a/gtk2_ardour/audio_trigger_properties_box.cc
+++ b/gtk2_ardour/audio_trigger_properties_box.cc
@@ -151,7 +151,7 @@ AudioTriggerPropertiesBox::AudioTriggerPropertiesBox ()
 	_beat_spinner.set_can_focus(false);
 	_beat_spinner.signal_changed ().connect (sigc::mem_fun (*this, &AudioTriggerPropertiesBox::beats_changed));
 
-	set_tooltip(_stretch_toggle, _("If enabled, the clip will be stretched to match the current timeline tempo"));
+	set_tooltip(_stretch_toggle, _("<b>If enabled</b>, the clip will be stretched to match the current timeline tempo"));
 	set_tooltip(_stretch_selector, _("Select Crisp for drum loops, Smooth for sustained notes, or Mixed if the clip has both"));
 	set_tooltip(_beat_spinner, _("Length of the clip, in beats. Changing this will change the tempo"));
 	set_tooltip(_half_button, _("Click to halve the tempo for the clip. This will result in it playing faster when stretched on the timeline"));
diff --git a/gtk2_ardour/editor_regions.cc b/gtk2_ardour/editor_regions.cc
index 4ffe2adbbb..f4220b9a6e 100644
--- a/gtk2_ardour/editor_regions.cc
+++ b/gtk2_ardour/editor_regions.cc
@@ -101,9 +101,9 @@ EditorRegions::init ()
 	tvc = append_col (_columns.sync, bbt_width);
 	setup_col (tvc, -1, ALIGN_RIGHT, _("Sync"), _("Position of region sync point, relative to start of the region"));
 	tvc = append_col (_columns.fadein, bbt_width);
-	setup_col (tvc, -1, ALIGN_RIGHT, _("Fade In"), _("Length of region fade-in (units: secondary clock, () if disabled"));
+	setup_col (tvc, -1, ALIGN_RIGHT, _("Fade In"), _("Length of region fade-in (unit: secondary clock, enclosed in parenthesis if the fade is disabled)"));
 	tvc = append_col (_columns.fadeout, bbt_width);
-	setup_col (tvc, -1, ALIGN_RIGHT, _("Fade out"), _("Length of region fade-out (units: secondary clock, () if disabled"));
+	setup_col (tvc, -1, ALIGN_RIGHT, _("Fade out"), _("Length of region fade-out (unit: secondary clock, enclosed in parenthesis if the fade is disabled)"));
 #endif
 }
 
diff --git a/gtk2_ardour/rc_option_editor.cc b/gtk2_ardour/rc_option_editor.cc
index 5687406b57..35226124d5 100644
--- a/gtk2_ardour/rc_option_editor.cc
+++ b/gtk2_ardour/rc_option_editor.cc
@@ -3452,7 +3452,7 @@ These settings will only take effect after %1 is restarted.\n\
 		     sigc::mem_fun (UIConfiguration::instance(), &UIConfiguration::set_name_new_markers)
 		);
 	add_option (_("Transport"), bo);
-	Gtkmm2ext::UI::instance()->set_tip (bo->tip_widget(), _("If enabled, popup a dialog when a new marker is created to allow its name to be set as it is created."
+	Gtkmm2ext::UI::instance()->set_tip (bo->tip_widget(), _("<b>When enabled</b>, popup a dialog when a new marker is created to allow its name to be set as it is created."
 								"\n\nYou can always rename markers by right-clicking on them."));
 
 	bo = new BoolOption (
@@ -3813,7 +3813,7 @@ These settings will only take effect after %1 is restarted.\n\
 		);
 	add_option (_("Plugins"), bo);
 	Gtkmm2ext::UI::instance()->set_tip (bo->tip_widget(),
-					    _("<b>When enabled</b> at most one plugin GUI window be on-screen at a time. When disabled, the number of visible plugin GUI windows is unlimited"));
+					    _("<b>When enabled</b> at most one plugin GUI window can be on-screen at a time. <b>When disabled</b>, the number of visible plugin GUI windows is unlimited"));
 
 #if (defined WINDOWS_VST_SUPPORT || defined MACVST_SUPPORT || defined LXVST_SUPPORT || defined VST3_SUPPORT)
 	add_option (_("Plugins/VST"), new OptionEditorHeading (_("VST")));
@@ -4693,8 +4693,8 @@ These settings will only take effect after %1 is restarted.\n\
 
 	TriggerPortSelectOption* dtip  = new TriggerPortSelectOption (_rc_config, this);
 
-	set_tooltip (dtip->tip_widget(), _("If set, the identifies the input MIDI port that will be automatically connected to trigger boxes.\n\n"
-	                                   "It is intended to be either an NxN pad device such as the Ableton Push 2 or Novation Launchpad\n"
+	set_tooltip (dtip->tip_widget(), _("If set, this identifies the input MIDI port that will be automatically connected to trigger boxes.\n\n"
+	                                   "It is intended to be connected to a NxN pad device (such as the Ableton Push 2 or Novation Launchpad)\n"
 	                                   "or a regular MIDI device capable of sending sequential note numbers (like a typical keyboard)"));
 	add_option (_("Triggering"), dtip);