diff --git a/src/lib/components/notes/Notes.svelte b/src/lib/components/notes/Notes.svelte
index 9bda19b6d6..786d03dd9a 100644
--- a/src/lib/components/notes/Notes.svelte
+++ b/src/lib/components/notes/Notes.svelte
@@ -320,11 +320,16 @@
 		dropzoneElement?.addEventListener('drop', onDrop);
 		dropzoneElement?.addEventListener('dragleave', onDragLeave);
 
+		let keyboardFocusedElement: Element | null = null;
+		const onFocusIn = (event: FocusEvent) => {
+			const target = event.target as Element;
+			keyboardFocusedElement = target.matches(':focus-visible:not(input, textarea)')
+				? target
+				: null;
+		};
+
 		const onKeyDown = (event: KeyboardEvent) => {
-			if (
-				event.key === 'Shift' &&
-				!document.activeElement?.matches(':focus-visible:not(input, textarea)')
-			) {
+			if (event.key === 'Shift' && document.activeElement !== keyboardFocusedElement) {
 				shiftKey = true;
 				openNoteMenuId = null;
 			}
@@ -340,6 +345,7 @@
 			shiftKey = false;
 		};
 
+		window.addEventListener('focusin', onFocusIn);
 		window.addEventListener('keydown', onKeyDown);
 		window.addEventListener('keyup', onKeyUp);
 		window.addEventListener('blur', onBlur);
@@ -347,6 +353,7 @@
 		return () => {
 			clearTimeout(searchDebounceTimer);
 
+			window.removeEventListener('focusin', onFocusIn);
 			window.removeEventListener('keydown', onKeyDown);
 			window.removeEventListener('keyup', onKeyUp);
 			window.removeEventListener('blur', onBlur);
diff --git a/src/lib/components/workspace/Models.svelte b/src/lib/components/workspace/Models.svelte
index 3d6bb28c07..4d2c7c757c 100644
--- a/src/lib/components/workspace/Models.svelte
+++ b/src/lib/components/workspace/Models.svelte
@@ -488,11 +488,16 @@
 		await tick();
 		loaded = true;
 
+		let keyboardFocusedElement: Element | null = null;
+		const onFocusIn = (event: FocusEvent) => {
+			const target = event.target as Element;
+			keyboardFocusedElement = target.matches(':focus-visible:not(input, textarea)')
+				? target
+				: null;
+		};
+
 		const onKeyDown = (event) => {
-			if (
-				event.key === 'Shift' &&
-				!document.activeElement?.matches(':focus-visible:not(input, textarea)')
-			) {
+			if (event.key === 'Shift' && document.activeElement !== keyboardFocusedElement) {
 				shiftKey = true;
 			}
 		};
@@ -507,11 +512,13 @@
 			shiftKey = false;
 		};
 
+		window.addEventListener('focusin', onFocusIn);
 		window.addEventListener('keydown', onKeyDown);
 		window.addEventListener('keyup', onKeyUp);
 		window.addEventListener('blur', onBlur);
 
 		return () => {
+			window.removeEventListener('focusin', onFocusIn);
 			window.removeEventListener('keydown', onKeyDown);
 			window.removeEventListener('keyup', onKeyUp);
 			window.removeEventListener('blur', onBlur);
diff --git a/src/lib/components/workspace/Prompts.svelte b/src/lib/components/workspace/Prompts.svelte
index cb0b663db0..7b1f627c68 100644
--- a/src/lib/components/workspace/Prompts.svelte
+++ b/src/lib/components/workspace/Prompts.svelte
@@ -351,11 +351,16 @@
 			openCreateModal();
 		}
 
+		let keyboardFocusedElement: Element | null = null;
+		const onFocusIn = (event: FocusEvent) => {
+			const target = event.target as Element;
+			keyboardFocusedElement = target.matches(':focus-visible:not(input, textarea)')
+				? target
+				: null;
+		};
+
 		const onKeyDown = (event: KeyboardEvent) => {
-			if (
-				event.key === 'Shift' &&
-				!document.activeElement?.matches(':focus-visible:not(input, textarea)')
-			) {
+			if (event.key === 'Shift' && document.activeElement !== keyboardFocusedElement) {
 				shiftKey = true;
 			}
 		};
@@ -370,6 +375,7 @@
 			shiftKey = false;
 		};
 
+		window.addEventListener('focusin', onFocusIn);
 		window.addEventListener('keydown', onKeyDown);
 		window.addEventListener('keyup', onKeyUp);
 		window.addEventListener('blur', onBlur);
@@ -377,6 +383,7 @@
 		return () => {
 			clearTimeout(searchDebounceTimer);
 			window.removeEventListener('message', onMessage);
+			window.removeEventListener('focusin', onFocusIn);
 			window.removeEventListener('keydown', onKeyDown);
 			window.removeEventListener('keyup', onKeyUp);
 			window.removeEventListener('blur', onBlur);
diff --git a/src/lib/components/workspace/Skills.svelte b/src/lib/components/workspace/Skills.svelte
index 4cb9cbc754..29ff9c3908 100644
--- a/src/lib/components/workspace/Skills.svelte
+++ b/src/lib/components/workspace/Skills.svelte
@@ -303,11 +303,16 @@
 		viewOption = localStorage?.workspaceViewOption || '';
 		loaded = true;
 
+		let keyboardFocusedElement: Element | null = null;
+		const onFocusIn = (event: FocusEvent) => {
+			const target = event.target as Element;
+			keyboardFocusedElement = target.matches(':focus-visible:not(input, textarea)')
+				? target
+				: null;
+		};
+
 		const onKeyDown = (event) => {
-			if (
-				event.key === 'Shift' &&
-				!document.activeElement?.matches(':focus-visible:not(input, textarea)')
-			) {
+			if (event.key === 'Shift' && document.activeElement !== keyboardFocusedElement) {
 				shiftKey = true;
 			}
 		};
@@ -322,12 +327,14 @@
 			shiftKey = false;
 		};
 
+		window.addEventListener('focusin', onFocusIn);
 		window.addEventListener('keydown', onKeyDown);
 		window.addEventListener('keyup', onKeyUp);
 		window.addEventListener('blur', onBlur);
 
 		return () => {
 			clearTimeout(searchDebounceTimer);
+			window.removeEventListener('focusin', onFocusIn);
 			window.removeEventListener('keydown', onKeyDown);
 			window.removeEventListener('keyup', onKeyUp);
 			window.removeEventListener('blur', onBlur);
diff --git a/src/lib/components/workspace/Tools.svelte b/src/lib/components/workspace/Tools.svelte
index 6684391a45..c02ef51976 100644
--- a/src/lib/components/workspace/Tools.svelte
+++ b/src/lib/components/workspace/Tools.svelte
@@ -299,11 +299,16 @@
 		await init();
 		loaded = true;
 
+		let keyboardFocusedElement: Element | null = null;
+		const onFocusIn = (event: FocusEvent) => {
+			const target = event.target as Element;
+			keyboardFocusedElement = target.matches(':focus-visible:not(input, textarea)')
+				? target
+				: null;
+		};
+
 		const onKeyDown = (event) => {
-			if (
-				event.key === 'Shift' &&
-				!document.activeElement?.matches(':focus-visible:not(input, textarea)')
-			) {
+			if (event.key === 'Shift' && document.activeElement !== keyboardFocusedElement) {
 				shiftKey = true;
 			}
 		};
@@ -318,12 +323,14 @@
 			shiftKey = false;
 		};
 
+		window.addEventListener('focusin', onFocusIn);
 		window.addEventListener('keydown', onKeyDown);
 		window.addEventListener('keyup', onKeyUp);
 		window.addEventListener('blur', onBlur);
 
 		return () => {
 			clearTimeout(searchDebounceTimer);
+			window.removeEventListener('focusin', onFocusIn);
 			window.removeEventListener('keydown', onKeyDown);
 			window.removeEventListener('keyup', onKeyUp);
 			window.removeEventListener('blur', onBlur);
diff --git a/src/routes/(app)/automations/+page.svelte b/src/routes/(app)/automations/+page.svelte
index 7cc3c7c47b..8598c8ad9d 100644
--- a/src/routes/(app)/automations/+page.svelte
+++ b/src/routes/(app)/automations/+page.svelte
@@ -324,11 +324,16 @@
 		loaded = true;
 		ensureChannels();
 
+		let keyboardFocusedElement: Element | null = null;
+		const onFocusIn = (event: FocusEvent) => {
+			const target = event.target as Element;
+			keyboardFocusedElement = target.matches(':focus-visible:not(input, textarea)')
+				? target
+				: null;
+		};
+
 		const onKeyDown = (event: KeyboardEvent) => {
-			if (
-				event.key === 'Shift' &&
-				!document.activeElement?.matches(':focus-visible:not(input, textarea)')
-			) {
+			if (event.key === 'Shift' && document.activeElement !== keyboardFocusedElement) {
 				shiftKey = true;
 				openAutomationMenuId = null;
 			}
@@ -344,6 +349,7 @@
 			shiftKey = false;
 		};
 
+		window.addEventListener('focusin', onFocusIn);
 		window.addEventListener('keydown', onKeyDown);
 		window.addEventListener('keyup', onKeyUp);
 		window.addEventListener('blur', onBlur);
@@ -351,6 +357,7 @@
 		return () => {
 			clearTimeout(searchDebounceTimer);
 
+			window.removeEventListener('focusin', onFocusIn);
 			window.removeEventListener('keydown', onKeyDown);
 			window.removeEventListener('keyup', onKeyUp);
 			window.removeEventListener('blur', onBlur);