diff --git a/web/src/components/card/ReviewCard.tsx b/web/src/components/card/ReviewCard.tsx
index 64f52bd1b..33032d2b8 100644
--- a/web/src/components/card/ReviewCard.tsx
+++ b/web/src/components/card/ReviewCard.tsx
@@ -6,7 +6,7 @@ import { getIconForLabel } from "@/utils/iconUtil";
 import { isDesktop, isIOS, isSafari } from "react-device-detect";
 import useSWR from "swr";
 import TimeAgo from "../dynamic/TimeAgo";
-import { useCallback, useMemo, useState } from "react";
+import { useCallback, useMemo, useRef, useState } from "react";
 import useImageLoaded from "@/hooks/use-image-loaded";
 import ImageLoadingIndicator from "../indicators/ImageLoadingIndicator";
 import { FaCompactDisc } from "react-icons/fa";
@@ -18,9 +18,20 @@ import {
   ContextMenuItem,
   ContextMenuTrigger,
 } from "../ui/context-menu";
+import {
+  AlertDialog,
+  AlertDialogAction,
+  AlertDialogCancel,
+  AlertDialogContent,
+  AlertDialogDescription,
+  AlertDialogFooter,
+  AlertDialogHeader,
+  AlertDialogTitle,
+} from "../ui/alert-dialog";
 import { Drawer, DrawerContent } from "../ui/drawer";
 import axios from "axios";
 import { toast } from "sonner";
+import useKeyboardListener from "@/hooks/use-keyboard-listener";
 
 type ReviewCardProps = {
   event: ReviewSegment;
@@ -46,6 +57,8 @@ export default function ReviewCard({
   );
 
   const [optionsOpen, setOptionsOpen] = useState(false);
+  const [deleteDialogOpen, setDeleteDialogOpen] = useState(false);
+  const bypassDialogRef = useRef(false);
 
   const onMarkAsReviewed = useCallback(async () => {
     await axios.post(`reviews/viewed`, { ids: [event.id] });
@@ -92,6 +105,18 @@ export default function ReviewCard({
     setOptionsOpen(false);
   }, [event]);
 
+  useKeyboardListener(["Shift"], (_, modifiers) => {
+    bypassDialogRef.current = modifiers.shift;
+  });
+
+  const handleDelete = useCallback(() => {
+    if (bypassDialogRef.current) {
+      onDelete();
+    } else {
+      setDeleteDialogOpen(true);
+    }
+  }, [bypassDialogRef, onDelete]);
+
   const content = (
     <div
       className="relative flex w-full cursor-pointer flex-col gap-1.5"
@@ -158,71 +183,129 @@ export default function ReviewCard({
 
   if (isDesktop) {
     return (
-      <ContextMenu>
-        <ContextMenuTrigger asChild>{content}</ContextMenuTrigger>
-        <ContextMenuContent>
-          <ContextMenuItem>
-            <div
-              className="flex w-full cursor-pointer items-center justify-start gap-2 p-2"
-              onClick={onExport}
-            >
-              <FaCompactDisc className="text-secondary-foreground" />
-              <div className="text-primary">Export</div>
-            </div>
-          </ContextMenuItem>
-          {!event.has_been_reviewed && (
+      <>
+        <AlertDialog
+          open={deleteDialogOpen}
+          onOpenChange={() => setDeleteDialogOpen(!deleteDialogOpen)}
+        >
+          <AlertDialogContent>
+            <AlertDialogHeader>
+              <AlertDialogTitle>Confirm Delete</AlertDialogTitle>
+            </AlertDialogHeader>
+            <AlertDialogDescription>
+              Are you sure you want to delete all recorded video associated with
+              this review item?
+              <br />
+              <br />
+              Hold the <em>Shift</em> key to bypass this dialog in the future.
+            </AlertDialogDescription>
+            <AlertDialogFooter>
+              <AlertDialogCancel onClick={() => setOptionsOpen(false)}>
+                Cancel
+              </AlertDialogCancel>
+              <AlertDialogAction className="bg-destructive" onClick={onDelete}>
+                Delete
+              </AlertDialogAction>
+            </AlertDialogFooter>
+          </AlertDialogContent>
+        </AlertDialog>
+        <ContextMenu key={event.id}>
+          <ContextMenuTrigger asChild>{content}</ContextMenuTrigger>
+          <ContextMenuContent>
             <ContextMenuItem>
               <div
                 className="flex w-full cursor-pointer items-center justify-start gap-2 p-2"
-                onClick={onMarkAsReviewed}
+                onClick={onExport}
               >
-                <FaCircleCheck className="text-secondary-foreground" />
-                <div className="text-primary">Mark as reviewed</div>
+                <FaCompactDisc className="text-secondary-foreground" />
+                <div className="text-primary">Export</div>
               </div>
             </ContextMenuItem>
-          )}
-          <ContextMenuItem>
-            <div
-              className="flex w-full cursor-pointer items-center justify-start gap-2 p-2"
-              onClick={onDelete}
-            >
-              <HiTrash className="text-secondary-foreground" />
-              <div className="text-primary">Delete</div>
-            </div>
-          </ContextMenuItem>
-        </ContextMenuContent>
-      </ContextMenu>
+            {!event.has_been_reviewed && (
+              <ContextMenuItem>
+                <div
+                  className="flex w-full cursor-pointer items-center justify-start gap-2 p-2"
+                  onClick={onMarkAsReviewed}
+                >
+                  <FaCircleCheck className="text-secondary-foreground" />
+                  <div className="text-primary">Mark as reviewed</div>
+                </div>
+              </ContextMenuItem>
+            )}
+            <ContextMenuItem>
+              <div
+                className="flex w-full cursor-pointer items-center justify-start gap-2 p-2"
+                onClick={handleDelete}
+              >
+                <HiTrash className="text-secondary-foreground" />
+                <div className="text-primary">
+                  {bypassDialogRef.current ? "Delete Now" : "Delete"}
+                </div>
+              </div>
+            </ContextMenuItem>
+          </ContextMenuContent>
+        </ContextMenu>
+      </>
     );
   }
 
   return (
-    <Drawer open={optionsOpen} onOpenChange={setOptionsOpen}>
-      {content}
-      <DrawerContent>
-        <div
-          className="flex w-full items-center justify-start gap-2 p-2"
-          onClick={onExport}
-        >
-          <FaCompactDisc className="text-secondary-foreground" />
-          <div className="text-primary">Export</div>
-        </div>
-        {!event.has_been_reviewed && (
+    <>
+      <AlertDialog
+        open={deleteDialogOpen}
+        onOpenChange={() => setDeleteDialogOpen(!deleteDialogOpen)}
+      >
+        <AlertDialogContent>
+          <AlertDialogHeader>
+            <AlertDialogTitle>Confirm Delete</AlertDialogTitle>
+          </AlertDialogHeader>
+          <AlertDialogDescription>
+            Are you sure you want to delete all recorded video associated with
+            this review item?
+            <br />
+            <br />
+            Hold the <em>Shift</em> key to bypass this dialog in the future.
+          </AlertDialogDescription>
+          <AlertDialogFooter>
+            <AlertDialogCancel onClick={() => setOptionsOpen(false)}>
+              Cancel
+            </AlertDialogCancel>
+            <AlertDialogAction className="bg-destructive" onClick={onDelete}>
+              Delete
+            </AlertDialogAction>
+          </AlertDialogFooter>
+        </AlertDialogContent>
+      </AlertDialog>
+      <Drawer open={optionsOpen} onOpenChange={setOptionsOpen}>
+        {content}
+        <DrawerContent>
           <div
             className="flex w-full items-center justify-start gap-2 p-2"
-            onClick={onMarkAsReviewed}
+            onClick={onExport}
           >
-            <FaCircleCheck className="text-secondary-foreground" />
-            <div className="text-primary">Mark as reviewed</div>
+            <FaCompactDisc className="text-secondary-foreground" />
+            <div className="text-primary">Export</div>
           </div>
-        )}
-        <div
-          className="flex w-full items-center justify-start gap-2 p-2"
-          onClick={onDelete}
-        >
-          <HiTrash className="text-secondary-foreground" />
-          <div className="text-primary">Delete</div>
-        </div>
-      </DrawerContent>
-    </Drawer>
+          {!event.has_been_reviewed && (
+            <div
+              className="flex w-full items-center justify-start gap-2 p-2"
+              onClick={onMarkAsReviewed}
+            >
+              <FaCircleCheck className="text-secondary-foreground" />
+              <div className="text-primary">Mark as reviewed</div>
+            </div>
+          )}
+          <div
+            className="flex w-full items-center justify-start gap-2 p-2"
+            onClick={handleDelete}
+          >
+            <HiTrash className="text-secondary-foreground" />
+            <div className="text-primary">
+              {bypassDialogRef.current ? "Delete Now" : "Delete"}
+            </div>
+          </div>
+        </DrawerContent>
+      </Drawer>
+    </>
   );
 }
diff --git a/web/src/components/filter/ReviewActionGroup.tsx b/web/src/components/filter/ReviewActionGroup.tsx
index 49e9f561a..c637b1e35 100644
--- a/web/src/components/filter/ReviewActionGroup.tsx
+++ b/web/src/components/filter/ReviewActionGroup.tsx
@@ -1,10 +1,21 @@
 import { FaCircleCheck } from "react-icons/fa6";
-import { useCallback } from "react";
+import { useCallback, useState } from "react";
 import axios from "axios";
 import { Button } from "../ui/button";
 import { isDesktop } from "react-device-detect";
 import { FaCompactDisc } from "react-icons/fa";
 import { HiTrash } from "react-icons/hi";
+import {
+  AlertDialog,
+  AlertDialogAction,
+  AlertDialogCancel,
+  AlertDialogContent,
+  AlertDialogDescription,
+  AlertDialogFooter,
+  AlertDialogHeader,
+  AlertDialogTitle,
+} from "../ui/alert-dialog";
+import useKeyboardListener from "@/hooks/use-keyboard-listener";
 
 type ReviewActionGroupProps = {
   selectedReviews: string[];
@@ -34,49 +45,94 @@ export default function ReviewActionGroup({
     pullLatestData();
   }, [selectedReviews, setSelectedReviews, pullLatestData]);
 
+  const [deleteDialogOpen, setDeleteDialogOpen] = useState(false);
+  const [bypassDialog, setBypassDialog] = useState(false);
+
+  useKeyboardListener(["Shift"], (_, modifiers) => {
+    setBypassDialog(modifiers.shift);
+  });
+
+  const handleDelete = useCallback(() => {
+    if (bypassDialog) {
+      onDelete();
+    } else {
+      setDeleteDialogOpen(true);
+    }
+  }, [bypassDialog, onDelete]);
+
   return (
-    <div className="absolute inset-x-2 inset-y-0 flex items-center justify-between gap-2 bg-background py-2 md:left-auto">
-      <div className="mx-1 flex items-center justify-center text-sm text-muted-foreground">
-        <div className="p-1">{`${selectedReviews.length} selected`}</div>
-        <div className="p-1">{"|"}</div>
-        <div
-          className="cursor-pointer p-2 text-primary hover:rounded-lg hover:bg-secondary"
-          onClick={onClearSelected}
-        >
-          Unselect
+    <>
+      <AlertDialog
+        open={deleteDialogOpen}
+        onOpenChange={() => setDeleteDialogOpen(!deleteDialogOpen)}
+      >
+        <AlertDialogContent>
+          <AlertDialogHeader>
+            <AlertDialogTitle>Confirm Delete</AlertDialogTitle>
+          </AlertDialogHeader>
+          <AlertDialogDescription>
+            Are you sure you want to delete all recorded video associated with
+            the selected review items?
+            <br />
+            <br />
+            Hold the <em>Shift</em> key to bypass this dialog in the future.
+          </AlertDialogDescription>
+          <AlertDialogFooter>
+            <AlertDialogCancel>Cancel</AlertDialogCancel>
+            <AlertDialogAction className="bg-destructive" onClick={onDelete}>
+              Delete
+            </AlertDialogAction>
+          </AlertDialogFooter>
+        </AlertDialogContent>
+      </AlertDialog>
+
+      <div className="absolute inset-x-2 inset-y-0 flex items-center justify-between gap-2 bg-background py-2 md:left-auto">
+        <div className="mx-1 flex items-center justify-center text-sm text-muted-foreground">
+          <div className="p-1">{`${selectedReviews.length} selected`}</div>
+          <div className="p-1">{"|"}</div>
+          <div
+            className="cursor-pointer p-2 text-primary hover:rounded-lg hover:bg-secondary"
+            onClick={onClearSelected}
+          >
+            Unselect
+          </div>
         </div>
-      </div>
-      <div className="flex items-center gap-1 md:gap-2">
-        {selectedReviews.length == 1 && (
+        <div className="flex items-center gap-1 md:gap-2">
+          {selectedReviews.length == 1 && (
+            <Button
+              className="flex items-center gap-2 p-2"
+              size="sm"
+              onClick={() => {
+                onExport(selectedReviews[0]);
+                onClearSelected();
+              }}
+            >
+              <FaCompactDisc className="text-secondary-foreground" />
+              {isDesktop && <div className="text-primary">Export</div>}
+            </Button>
+          )}
           <Button
             className="flex items-center gap-2 p-2"
             size="sm"
-            onClick={() => {
-              onExport(selectedReviews[0]);
-              onClearSelected();
-            }}
+            onClick={onMarkAsReviewed}
           >
-            <FaCompactDisc className="text-secondary-foreground" />
-            {isDesktop && <div className="text-primary">Export</div>}
+            <FaCircleCheck className="text-secondary-foreground" />
+            {isDesktop && <div className="text-primary">Mark as reviewed</div>}
           </Button>
-        )}
-        <Button
-          className="flex items-center gap-2 p-2"
-          size="sm"
-          onClick={onMarkAsReviewed}
-        >
-          <FaCircleCheck className="text-secondary-foreground" />
-          {isDesktop && <div className="text-primary">Mark as reviewed</div>}
-        </Button>
-        <Button
-          className="flex items-center gap-2 p-2"
-          size="sm"
-          onClick={onDelete}
-        >
-          <HiTrash className="text-secondary-foreground" />
-          {isDesktop && <div className="text-primary">Delete</div>}
-        </Button>
+          <Button
+            className="flex items-center gap-2 p-2"
+            size="sm"
+            onClick={handleDelete}
+          >
+            <HiTrash className="text-secondary-foreground" />
+            {isDesktop && (
+              <div className="text-primary">
+                {bypassDialog ? "Delete Now" : "Delete"}
+              </div>
+            )}
+          </Button>
+        </div>
       </div>
-    </div>
+    </>
   );
 }
diff --git a/web/src/components/player/VideoControls.tsx b/web/src/components/player/VideoControls.tsx
index 70d9a4be8..50b2cc045 100644
--- a/web/src/components/player/VideoControls.tsx
+++ b/web/src/components/player/VideoControls.tsx
@@ -141,7 +141,7 @@ export default function VideoControls({
   }, [volume, muted]);
 
   const onKeyboardShortcut = useCallback(
-    (key: string, modifiers: KeyModifiers) => {
+    (key: string | null, modifiers: KeyModifiers) => {
       if (!modifiers.down) {
         return;
       }
diff --git a/web/src/hooks/use-keyboard-listener.tsx b/web/src/hooks/use-keyboard-listener.tsx
index f127cf0d8..ad9462a05 100644
--- a/web/src/hooks/use-keyboard-listener.tsx
+++ b/web/src/hooks/use-keyboard-listener.tsx
@@ -4,11 +4,12 @@ export type KeyModifiers = {
   down: boolean;
   repeat: boolean;
   ctrl: boolean;
+  shift: boolean;
 };
 
 export default function useKeyboardListener(
   keys: string[],
-  listener: (key: string, modifiers: KeyModifiers) => void,
+  listener: (key: string | null, modifiers: KeyModifiers) => void,
 ) {
   const keyDownListener = useCallback(
     (e: KeyboardEvent) => {
@@ -16,13 +17,18 @@ export default function useKeyboardListener(
         return;
       }
 
+      const modifiers = {
+        down: true,
+        repeat: e.repeat,
+        ctrl: e.ctrlKey || e.metaKey,
+        shift: e.shiftKey,
+      };
+
       if (keys.includes(e.key)) {
         e.preventDefault();
-        listener(e.key, {
-          down: true,
-          repeat: e.repeat,
-          ctrl: e.ctrlKey || e.metaKey,
-        });
+        listener(e.key, modifiers);
+      } else if (e.key === "Shift" || e.key === "Control" || e.key === "Meta") {
+        listener(null, modifiers);
       }
     },
     [keys, listener],
@@ -34,9 +40,18 @@ export default function useKeyboardListener(
         return;
       }
 
+      const modifiers = {
+        down: false,
+        repeat: false,
+        ctrl: false,
+        shift: false,
+      };
+
       if (keys.includes(e.key)) {
         e.preventDefault();
-        listener(e.key, { down: false, repeat: false, ctrl: false });
+        listener(e.key, modifiers);
+      } else if (e.key === "Shift" || e.key === "Control" || e.key === "Meta") {
+        listener(null, modifiers);
       }
     },
     [keys, listener],
diff --git a/web/src/views/live/LiveDashboardView.tsx b/web/src/views/live/LiveDashboardView.tsx
index 51f46d2f2..a91afb356 100644
--- a/web/src/views/live/LiveDashboardView.tsx
+++ b/web/src/views/live/LiveDashboardView.tsx
@@ -31,9 +31,7 @@ import { cn } from "@/lib/utils";
 import { LivePlayerError, LivePlayerMode } from "@/types/live";
 import { FaCompress, FaExpand } from "react-icons/fa";
 import { useResizeObserver } from "@/hooks/resize-observer";
-import useKeyboardListener, {
-  KeyModifiers,
-} from "@/hooks/use-keyboard-listener";
+import useKeyboardListener from "@/hooks/use-keyboard-listener";
 
 type LiveDashboardViewProps = {
   cameras: CameraConfig[];
@@ -250,22 +248,17 @@ export default function LiveDashboardView({
     [setPreferredLiveModes],
   );
 
-  const onKeyboardShortcut = useCallback(
-    (key: string, modifiers: KeyModifiers) => {
-      if (!modifiers.down) {
-        return;
-      }
+  useKeyboardListener(["f"], (key, modifiers) => {
+    if (!modifiers.down) {
+      return;
+    }
 
-      switch (key) {
-        case "f":
-          toggleFullscreen();
-          break;
-      }
-    },
-    [toggleFullscreen],
-  );
-
-  useKeyboardListener(["f"], onKeyboardShortcut);
+    switch (key) {
+      case "f":
+        toggleFullscreen();
+        break;
+    }
+  });
 
   return (
     <div