diff --git a/src/components/MainContent.tsx b/src/components/MainContent.tsx
index 00bc552..a6edb06 100644
--- a/src/components/MainContent.tsx
+++ b/src/components/MainContent.tsx
@@ -4,12 +4,13 @@ import { createPortal } from 'react-dom';
 import { useProjectStore } from '../stores/projectStore';
 import { KGCore } from '../core/KGCore';
 import { KGTrack } from '../core/track/KGTrack';
+import { KGRegion } from '../core/region/KGRegion';
 import { KGMidiRegion } from '../core/region/KGMidiRegion';
 import { KGAudioRegion } from '../core/region/KGAudioRegion';
 import TrackInfoPanel from './track/TrackInfoPanel';
 import TrackGridPanel from './track/TrackGridPanel';
 import PianoRoll from './piano-roll/PianoRoll';
-import type { RegionUI } from './interfaces';
+import type { RegionClickOptions, RegionUI } from './interfaces';
 import { DEBUG_MODE, BAR_NUMBERS_CONSTANTS, TOOLBAR_CONSTANTS } from '../constants';
 import { useRegionOperations } from '../hooks/useRegionOperations';
 import { regionDeleteManager } from '../util/regionDeleteUtil';
@@ -38,6 +39,7 @@ const MainContent: React.FC<MainContentProps> = ({
     setAutoScrollEnabled,
     clearAllSelections,
     setSelectedTrack,
+    selectedRegionIds,
     showPianoRoll,
     activeRegionId,
     setShowPianoRoll,
@@ -349,7 +351,7 @@ const MainContent: React.FC<MainContentProps> = ({
       const updatedRegions = [...prevRegions, regionUI];
 
       // Select the region using the updated regions array
-      selectRegion(regionUI.id, updatedRegions);
+      selectRegion(regionUI.id, { shiftKey: false }, updatedRegions);
 
       // Manually trigger selection sync to ensure UI updates immediately
       const { syncSelectionFromCore } = useProjectStore.getState();
@@ -384,7 +386,7 @@ const MainContent: React.FC<MainContentProps> = ({
 
     setRegions(prev => {
       const updated = [...prev, regionUI];
-      selectRegion(regionUI.id, updated);
+      selectRegion(regionUI.id, { shiftKey: false }, updated);
       return updated;
     });
   };
@@ -518,10 +520,11 @@ const MainContent: React.FC<MainContentProps> = ({
   };
 
   // Helper function to select a region (clears previous selections)
-  const selectRegion = (regionId: string, regionsToSearch?: RegionUI[]) => {
-    // Clear any existing selections using store method
-    clearAllSelections();
-
+  const selectRegion = (
+    regionId: string,
+    options: RegionClickOptions = { shiftKey: false },
+    regionsToSearch?: RegionUI[]
+  ) => {
     // Find the region in the UI state (use provided regions or current state)
     const regionsToUse = regionsToSearch || regions;
     const region = regionsToUse.find(r => r.id === regionId);
@@ -542,39 +545,81 @@ const MainContent: React.FC<MainContentProps> = ({
     }
 
     // Find the region in the track's model
-    const trackRegions = track.getRegions();
-    const midiRegion = trackRegions.find(r => r.getId() === regionId) as KGMidiRegion | undefined;
+    const coreRegion = track.getRegions().find(r => r.getId() === regionId);
 
-    if (!midiRegion) {
+    if (!coreRegion) {
       if (DEBUG_MODE.MAIN_CONTENT) {
-        console.log(`MIDI region not found in track model: ${regionId}`);
+        console.log(`Region not found in track model: ${regionId}`);
       }
       return;
     }
 
-    // Add the region to KGCore's selection
     const core = KGCore.instance();
-    core.addSelectedItem(midiRegion);
+    const orderedSelection = options.shiftKey
+      ? (selectedRegionIds.includes(regionId)
+        ? selectedRegionIds.filter(id => id !== regionId)
+        : [...selectedRegionIds, regionId])
+      : [regionId];
 
-    // Update the region's internal selection state
-    midiRegion.select();
+    tracks.forEach(projectTrack => {
+      projectTrack.getRegions().forEach(projectRegion => projectRegion.deselect());
+    });
 
-    // Set the selected region (this might be redundant now, but keeping for compatibility)
-    setSelectedRegionId(regionId);
+    clearAllSelections();
+
+    const selectedRegions: KGRegion[] = orderedSelection
+      .map(selectedId => {
+        for (const projectTrack of tracks) {
+          const selectedRegion = projectTrack.getRegions().find(r => r.getId() === selectedId);
+          if (selectedRegion) {
+            selectedRegion.select();
+            return selectedRegion as KGRegion;
+          }
+        }
+        return null;
+      })
+      .filter((selectedRegion): selectedRegion is KGRegion => selectedRegion !== null);
+
+    if (selectedRegions.length > 0) {
+      core.addSelectedItems(selectedRegions);
+    }
+
+    const lastSelectedRegionId = selectedRegions.length > 0
+      ? selectedRegions[selectedRegions.length - 1].getId()
+      : null;
+
+    setSelectedRegionId(lastSelectedRegionId);
 
     if (DEBUG_MODE.MAIN_CONTENT) {
-      console.log(`Selected region: ${regionId} (added to KGCore selection)`);
+      console.log(`Selected regions: ${selectedRegions.map(selectedRegion => selectedRegion.getId()).join(', ')}`);
+    }
+
+    if (!showPianoRoll) {
+      return;
+    }
+
+    if (!lastSelectedRegionId) {
+      setShowPianoRoll(false);
+      setActiveRegionId(null);
+      return;
+    }
+
+    const lastSelectedRegion = selectedRegions[selectedRegions.length - 1];
+    if (lastSelectedRegion instanceof KGAudioRegion) {
+      openSpectrogramViewer(lastSelectedRegionId);
+    } else if (lastSelectedRegion instanceof KGMidiRegion) {
+      openMidiPianoRoll(lastSelectedRegionId);
     }
   };
 
   // Handle region single click: selection only (no piano roll opening)
-  const handleRegionClick = (regionId: string) => {
+  const handleRegionClick = (regionId: string, options: RegionClickOptions = { shiftKey: false }) => {
     if (DEBUG_MODE.MAIN_CONTENT) {
       console.log(`Region clicked in MainContent (selection only): ${regionId}`);
     }
 
     // Select the region
-    selectRegion(regionId);
+    selectRegion(regionId, options);
 
     // Also select the containing track
     const region = regions.find(r => r.id === regionId);
@@ -583,15 +628,6 @@ const MainContent: React.FC<MainContentProps> = ({
     if (!track) return;
     setSelectedTrack(track.getId().toString());
 
-    // If the piano roll window is already open, follow the selected region's type
-    if (showPianoRoll) {
-      const coreRegion = track.getRegions().find(r => r.getId() === regionId);
-      if (coreRegion?.getCurrentType() === 'KGAudioRegion') {
-        openSpectrogramViewer(regionId);
-      } else if (coreRegion?.getCurrentType() === 'KGMidiRegion') {
-        openMidiPianoRoll(regionId);
-      }
-    }
   };
 
   // Handle explicit pencil action: select region and open piano roll
@@ -610,7 +646,7 @@ const MainContent: React.FC<MainContentProps> = ({
     }
 
     // Reuse selection logic
-    handleRegionClick(regionId);
+    handleRegionClick(regionId, { shiftKey: false });
 
     // Activate and show piano roll in midi-edit mode
     openMidiPianoRoll(regionId);
@@ -618,7 +654,7 @@ const MainContent: React.FC<MainContentProps> = ({
 
   // Handle spectrogram viewer open
   const handleOpenSpectrogram = (regionId: string) => {
-    handleRegionClick(regionId);
+    handleRegionClick(regionId, { shiftKey: false });
     openSpectrogramViewer(regionId);
   };
 
diff --git a/src/components/Toolbar.tsx b/src/components/Toolbar.tsx
index d4f12a5..f2b076c 100644
--- a/src/components/Toolbar.tsx
+++ b/src/components/Toolbar.tsx
@@ -94,6 +94,7 @@ const Toolbar: React.FC = () => {
   
   // Export options
   const exportOptions = ["Export to KGStudio file", "Export to MIDI file", "Export to WAV", "Export to MP3"];
+  const lastSelectedRegionId = selectedRegionIds[selectedRegionIds.length - 1] ?? null;
 
   const handleProjectNameClick = async () => {
     const newName = await showPrompt("Enter project name:", projectName);
@@ -730,7 +731,7 @@ const Toolbar: React.FC = () => {
       return;
     }
 
-    const regionId = selectedRegionIds[0];
+    const regionId = lastSelectedRegionId;
     const tracks = KGCore.instance().getCurrentProject().getTracks();
     let targetRegion = null;
     for (const track of tracks) {
@@ -845,7 +846,7 @@ const Toolbar: React.FC = () => {
     }
 
     // Prefer current active region; otherwise, first selected region
-    const candidateRegionId = activeRegionId || (selectedRegionIds && selectedRegionIds.length > 0 ? selectedRegionIds[0] : null);
+    const candidateRegionId = activeRegionId || lastSelectedRegionId;
 
     if (!candidateRegionId) {
       if (DEBUG_MODE.TOOLBAR) {
@@ -877,7 +878,7 @@ const Toolbar: React.FC = () => {
     }
 
     // Require an active or selected MIDI region
-    const candidateId = activeRegionId ?? (selectedRegionIds[0] ?? null);
+    const candidateId = activeRegionId ?? lastSelectedRegionId;
     if (!candidateId) {
       await showAlert("Please open a MIDI region in the Piano Roll before starting recording.");
       return;
diff --git a/src/components/interfaces.ts b/src/components/interfaces.ts
index 9c6cbf1..5451700 100644
--- a/src/components/interfaces.ts
+++ b/src/components/interfaces.ts
@@ -18,6 +18,10 @@ export interface RegionUI {
   name: string;
 }
 
+export interface RegionClickOptions {
+  shiftKey: boolean;
+}
+
 // Define resize action types
 export type ResizeAction = 'none' | 'start' | 'end';
 
@@ -39,4 +43,4 @@ export interface RegionDragState {
   initialY: number;
   initialBarNumber: number;
   initialTrackIndex: number;
-} 
\ No newline at end of file
+} 
diff --git a/src/components/track/Region.css b/src/components/track/Region.css
index ef43a56..620911c 100644
--- a/src/components/track/Region.css
+++ b/src/components/track/Region.css
@@ -24,6 +24,10 @@
   border-color: #ffffff;
 }
 
+.track-region.selected-secondary {
+  border-color: rgba(255, 255, 255, 0.7);
+}
+
 .track-region.dragging {
   opacity: 0.8;
   box-shadow: 0 0 10px rgba(0, 0, 0, 0.5);
@@ -89,6 +93,10 @@
   border-color: #ffffff;
 }
 
+.track-region.audio-region.selected-secondary {
+  border-color: rgba(255, 255, 255, 0.7);
+}
+
 .track-region.audio-region .region-header {
   background-color: #4a8b5a;
 }
diff --git a/src/components/track/RegionItem.test.tsx b/src/components/track/RegionItem.test.tsx
index 7172df7..ee903b9 100644
--- a/src/components/track/RegionItem.test.tsx
+++ b/src/components/track/RegionItem.test.tsx
@@ -68,12 +68,25 @@ describe('RegionItem', () => {
     fireEvent.mouseMove(document, { clientX: 102, clientY: 102 });
     fireEvent.mouseUp(document, { clientX: 102, clientY: 102 });
 
-    expect(onClick).toHaveBeenCalledWith('midi-1');
+    expect(onClick).toHaveBeenCalledWith('midi-1', { shiftKey: false });
     expect(onDragStart).not.toHaveBeenCalled();
     expect(onDrag).not.toHaveBeenCalled();
     expect(onDragEnd).not.toHaveBeenCalled();
   });
 
+  it('passes shift-click state through the region click callback', () => {
+    const onClick = vi.fn();
+    const { container } = renderRegion({ onClick });
+    const region = container.querySelector('.track-region');
+
+    expect(region).toBeTruthy();
+
+    fireEvent.mouseDown(region!, { clientX: 100, clientY: 100, shiftKey: true });
+    fireEvent.mouseUp(document, { clientX: 100, clientY: 100, shiftKey: true });
+
+    expect(onClick).toHaveBeenCalledWith('midi-1', { shiftKey: true });
+  });
+
   it('starts a drag after crossing the movement threshold', () => {
     const onClick = vi.fn();
     const onDragStart = vi.fn();
diff --git a/src/components/track/RegionItem.tsx b/src/components/track/RegionItem.tsx
index 934a9b2..81072b5 100644
--- a/src/components/track/RegionItem.tsx
+++ b/src/components/track/RegionItem.tsx
@@ -2,7 +2,7 @@ import React, { useState, useRef, useEffect } from 'react';
 import './Region.css';
 import { FaPencilAlt, FaPlus } from 'react-icons/fa';
 import { MdGraphicEq, MdSwapHoriz } from 'react-icons/md';
-import type { ResizeAction } from '../interfaces';
+import type { RegionClickOptions, ResizeAction } from '../interfaces';
 import { REGION_CONSTANTS, DEBUG_MODE } from '../../constants';
 import { KGMidiRegion } from '../../core/region/KGMidiRegion';
 import { KGAudioRegion } from '../../core/region/KGAudioRegion';
@@ -27,7 +27,7 @@ interface RegionItemProps {
   onDrag?: (regionId: string, deltaX: number, deltaY: number) => void;
   onDragEnd?: (regionId: string) => void;
   // Click prop
-  onClick?: (regionId: string) => void;
+  onClick?: (regionId: string, options: RegionClickOptions) => void;
   // Explicit open piano roll action from header pencil icon
   onOpenPianoRoll?: (regionId: string) => void;
   // Open spectrogram viewer for audio regions
@@ -70,6 +70,7 @@ const RegionItem: React.FC<RegionItemProps> = ({
   // Get selection state and time signature from store
   const { selectedRegionIds, timeSignature, bpm } = useProjectStore();
   const isSelected = selectedRegionIds.includes(id);
+  const isPrimarySelected = isSelected && selectedRegionIds[selectedRegionIds.length - 1] === id;
   const [cursor, setCursor] = useState<string>('pointer');
   const [resizeEdge, setResizeEdge] = useState<ResizeAction>('none');
   const [isResizing, setIsResizing] = useState(false);
@@ -408,7 +409,7 @@ const RegionItem: React.FC<RegionItemProps> = ({
         if (DEBUG_MODE.REGION_ITEM) {
           console.log(`REGION CLICKED (pencil mode): regionId=${id}`);
         }
-        onClick(id);
+        onClick(id, { shiftKey: e.shiftKey });
       }
       return;
     }
@@ -535,7 +536,7 @@ const RegionItem: React.FC<RegionItemProps> = ({
       if (DEBUG_MODE.REGION_ITEM) {
         console.log(`REGION CLICKED: regionId=${id}`);
       }
-      onClick(id);
+      onClick(id, { shiftKey: e.shiftKey });
     }
 
     isPendingDragRef.current = false;
@@ -602,7 +603,7 @@ const RegionItem: React.FC<RegionItemProps> = ({
   return (
     <div
       key={id}
-      className={`track-region ${isDragging ? 'dragging' : ''} ${isSelected ? 'selected' : ''} ${audioRegion ? 'audio-region' : ''}`}
+      className={`track-region ${isDragging ? 'dragging' : ''} ${isSelected ? (isPrimarySelected ? 'selected' : 'selected-secondary') : ''} ${audioRegion ? 'audio-region' : ''}`}
       style={{ ...style, cursor, ...(isFineDragging ? { transform: `translateX(${fineTranslateX}px)`, zIndex: 100 } : {}) }}
       onMouseMove={handleMouseMove}
       onMouseLeave={handleMouseLeave}
@@ -634,7 +635,7 @@ const RegionItem: React.FC<RegionItemProps> = ({
                 if (onOpenPianoRoll) {
                   onOpenPianoRoll(id);
                 } else if (onClick) {
-                  onClick(id);
+                  onClick(id, { shiftKey: e.shiftKey });
                 }
               }}
               aria-label="Open piano roll"
diff --git a/src/components/track/TrackGridItem.tsx b/src/components/track/TrackGridItem.tsx
index dbb758c..f8c187b 100644
--- a/src/components/track/TrackGridItem.tsx
+++ b/src/components/track/TrackGridItem.tsx
@@ -4,7 +4,7 @@ import { KGMidiRegion } from '../../core/region/KGMidiRegion';
 import { KGAudioRegion } from '../../core/region/KGAudioRegion';
 import { KGAudioInterface } from '../../core/audio-interface/KGAudioInterface';
 import RegionItem from './RegionItem';
-import type { RegionUI, ResizeAction } from '../interfaces';
+import type { RegionClickOptions, RegionUI, ResizeAction } from '../interfaces';
 import { REGION_CONSTANTS, DEBUG_MODE } from '../../constants';
 import { KGMainContentState } from '../../core/state/KGMainContentState';
 import { isModifierKeyPressed } from '../../util/osUtil';
@@ -25,7 +25,7 @@ interface TrackGridItemProps {
   onRegionDrag?: (regionId: string, newBarNumber: number, newTrackIndex: number) => void;
   onRegionDragEnd?: (regionId: string, finalBarNumber: number, finalTrackIndex: number) => void;
   onRegionFineMoveEnd?: (regionId: string, deltaInBars: number) => void;
-  onRegionClick?: (regionId: string) => void;
+  onRegionClick?: (regionId: string, options: RegionClickOptions) => void;
   onOpenPianoRoll?: (regionId: string) => void;
   onOpenSpectrogram?: (regionId: string) => void;
   showHybridButtonForAudio?: boolean;
@@ -516,13 +516,13 @@ const TrackGridItem: React.FC<TrackGridItemProps> = ({
   };
 
   // Handle region click
-  const handleRegionClick = (regionId: string) => {
+  const handleRegionClick = (regionId: string, options: RegionClickOptions) => {
     if (DEBUG_MODE.TRACK_GRID_ITEM) {
       console.log(`Region clicked: ${regionId}`);
     }
     
     if (onRegionClick) {
-      onRegionClick(regionId);
+      onRegionClick(regionId, options);
     }
   };
 
@@ -589,7 +589,7 @@ const TrackGridItem: React.FC<TrackGridItemProps> = ({
                 onOpenPianoRoll(regionId);
               } else if (onRegionClick) {
                 // Fallback to legacy behavior
-                onRegionClick(regionId);
+                onRegionClick(regionId, { shiftKey: false });
               }
             }}
             onOpenSpectrogram={audioRegion ? (regionId) => {
diff --git a/src/components/track/TrackGridPanel.tsx b/src/components/track/TrackGridPanel.tsx
index c506142..e186464 100644
--- a/src/components/track/TrackGridPanel.tsx
+++ b/src/components/track/TrackGridPanel.tsx
@@ -3,7 +3,7 @@ import { KGTrack, TrackType } from '../../core/track/KGTrack';
 import { KGMidiRegion } from '../../core/region/KGMidiRegion';
 import TrackGridItem from './TrackGridItem';
 import { Playhead, FileImportModal } from '../common';
-import type { RegionUI } from '../interfaces';
+import type { RegionClickOptions, RegionUI } from '../interfaces';
 import { DEBUG_MODE, REGION_CONSTANTS } from '../../constants';
 import { KGMainContentState } from '../../core/state/KGMainContentState';
 import { isModifierKeyPressed } from '../../util/osUtil';
@@ -28,7 +28,7 @@ interface TrackGridPanelProps {
   projectName: string;
   onRegionCreated: (trackIndex: number, region: RegionUI, midiRegion: KGMidiRegion) => void;
   onRegionUpdated?: (regionId: string, updates: Partial<RegionUI>, expectedModelUpdates?: { startBeat: number, length: number }) => void;
-  onRegionClick?: (regionId: string) => void;
+  onRegionClick?: (regionId: string, options: RegionClickOptions) => void;
   onOpenPianoRoll?: (regionId: string) => void;
   onOpenSpectrogram?: (regionId: string) => void;
   showHybridButtonForAudio?: boolean;
@@ -512,7 +512,7 @@ const TrackGridPanel: React.FC<TrackGridPanelProps> = ({
   };
 
   // Handle region click
-  const handleRegionClick = (regionId: string) => {
+  const handleRegionClick = (regionId: string, options: RegionClickOptions) => {
     if (DEBUG_MODE.TRACK_GRID_PANEL) {
       console.log(`Region clicked in panel: ${regionId}`);
     }
@@ -535,7 +535,7 @@ const TrackGridPanel: React.FC<TrackGridPanelProps> = ({
     
     // Notify parent about the click
     if (onRegionClick) {
-      onRegionClick(regionId);
+      onRegionClick(regionId, options);
     }
   };
 
diff --git a/src/core/KGCore.ts b/src/core/KGCore.ts
index 6864a7b..23073ae 100644
--- a/src/core/KGCore.ts
+++ b/src/core/KGCore.ts
@@ -450,11 +450,14 @@ export class KGCore {
   }
 
   public addSelectedItem(item: Selectable): void {
+    this.selectedItems = this.selectedItems.filter(i => i.getId() !== item.getId());
     this.selectedItems.push(item);
     this.notifySelectionChanged();
   }
 
   public addSelectedItems(items: Selectable[]): void {
+    const seenIds = new Set(items.map(item => item.getId()));
+    this.selectedItems = this.selectedItems.filter(item => !seenIds.has(item.getId()));
     this.selectedItems.push(...items);
     this.notifySelectionChanged();
   }
diff --git a/src/hooks/useGlobalKeyboardHandler.ts b/src/hooks/useGlobalKeyboardHandler.ts
index 63d6e7a..f2d7c90 100644
--- a/src/hooks/useGlobalKeyboardHandler.ts
+++ b/src/hooks/useGlobalKeyboardHandler.ts
@@ -16,6 +16,7 @@ import { showAlert } from '../util/dialogUtil';
  */
 export const useGlobalKeyboardHandler = () => {
   const { undo, redo, setStatus, isPlaying, startPlaying, stopTransport, toggleLoop, projectName, savedProjectName, setSavedProjectName, setProjectName, isRecording, startRecording, stopRecording, activeRegionId, selectedRegionIds, setActiveRegionId, setShowPianoRoll, showPianoRoll, openMidiPianoRoll, openSpectrogramViewer } = useProjectStore();
+  const lastSelectedRegionId = selectedRegionIds[selectedRegionIds.length - 1] ?? null;
 
   useEffect(() => {
     const handleKeyDown = (event: KeyboardEvent) => {
@@ -166,7 +167,7 @@ export const useGlobalKeyboardHandler = () => {
           setStatus('Recording stopped — notes committed');
           return;
         }
-        const candidateId = activeRegionId ?? (selectedRegionIds[0] ?? null);
+        const candidateId = activeRegionId ?? lastSelectedRegionId;
         if (!candidateId) {
           setStatus('Select a MIDI region before recording');
           return;
@@ -201,7 +202,7 @@ export const useGlobalKeyboardHandler = () => {
           setShowPianoRoll(false);
           return;
         }
-        const candidateId = activeRegionId ?? (selectedRegionIds[0] ?? null);
+        const candidateId = activeRegionId ?? lastSelectedRegionId;
         if (!candidateId) {
           void showAlert('Please select a region to open the editor.');
           return;
@@ -264,7 +265,7 @@ export const useGlobalKeyboardHandler = () => {
     startRecording,
     stopRecording,
     activeRegionId,
-    selectedRegionIds,
+    lastSelectedRegionId,
     setActiveRegionId,
     setShowPianoRoll,
     showPianoRoll,