diff --git a/web/src/lib/components/assets/thumbnail/thumbnail.svelte b/web/src/lib/components/assets/thumbnail/thumbnail.svelte
index 87c54942d5..68131f67e0 100644
--- a/web/src/lib/components/assets/thumbnail/thumbnail.svelte
+++ b/web/src/lib/components/assets/thumbnail/thumbnail.svelte
@@ -84,9 +84,7 @@
         {#if !readonly && (mouseOver || selected || selectionCandidate)}
           <button
             on:click={onIconClickedHandler}
-            on:keydown|preventDefault
-            on:keyup|preventDefault
-            class="absolute p-2"
+            class="absolute p-2 focus:outline-none"
             class:cursor-not-allowed={disabled}
             role="checkbox"
             aria-checked={selected}
diff --git a/web/src/lib/components/photos-page/asset-date-group.svelte b/web/src/lib/components/photos-page/asset-date-group.svelte
index c7dc0b67a1..c39f377915 100644
--- a/web/src/lib/components/photos-page/asset-date-group.svelte
+++ b/web/src/lib/components/photos-page/asset-date-group.svelte
@@ -9,15 +9,15 @@
   } from '$lib/stores/asset-interaction.store';
   import { assetStore } from '$lib/stores/assets.store';
   import { locale } from '$lib/stores/preferences.store';
+  import { getAssetRatio } from '$lib/utils/asset-utils';
+  import { formatGroupTitle, splitBucketIntoDateGroups } from '$lib/utils/timeline-util';
   import type { AssetResponseDto } from '@api';
   import justifiedLayout from 'justified-layout';
-  import lodash from 'lodash-es';
+  import { DateTime } from 'luxon';
   import { createEventDispatcher } from 'svelte';
   import CheckCircle from 'svelte-material-icons/CheckCircle.svelte';
   import CircleOutline from 'svelte-material-icons/CircleOutline.svelte';
   import { fly } from 'svelte/transition';
-  import { DateTime, Interval } from 'luxon';
-  import { getAssetRatio } from '$lib/utils/asset-utils';
   import Thumbnail from '../assets/thumbnail/thumbnail.svelte';
 
   export let assets: AssetResponseDto[];
@@ -26,13 +26,6 @@
   export let isAlbumSelectionMode = false;
   export let viewportWidth: number;
 
-  const groupDateFormat: Intl.DateTimeFormatOptions = {
-    weekday: 'short',
-    month: 'short',
-    day: 'numeric',
-    year: 'numeric',
-  };
-
   const dispatch = createEventDispatcher();
 
   let isMouseOverGroup = false;
@@ -45,11 +38,7 @@
     width: number;
   }
 
-  $: assetsGroupByDate = lodash
-    .chain(assets)
-    .groupBy((a) => new Date(a.fileCreatedAt).toLocaleDateString($locale, groupDateFormat))
-    .sortBy((group) => assets.indexOf(group[0]))
-    .value();
+  $: assetsGroupByDate = splitBucketIntoDateGroups(assets, $locale);
 
   $: geometry = (() => {
     const geometry = [];
@@ -131,17 +120,7 @@
     assetsInDateGroup: AssetResponseDto[],
     dateGroupTitle: string,
   ) => {
-    if ($selectedAssets.has(asset)) {
-      for (const candidate of $assetSelectionCandidates || []) {
-        assetInteractionStore.removeAssetFromMultiselectGroup(candidate);
-      }
-      assetInteractionStore.removeAssetFromMultiselectGroup(asset);
-    } else {
-      for (const candidate of $assetSelectionCandidates || []) {
-        assetInteractionStore.addAssetToMultiselectGroup(candidate);
-      }
-      assetInteractionStore.addAssetToMultiselectGroup(asset);
-    }
+    dispatch('selectAssets', { asset });
 
     // Check if all assets are selected in a group to toggle the group selection's icon
     let selectedAssetsInGroupCount = assetsInDateGroup.filter((asset) => $selectedAssets.has(asset)).length;
@@ -162,41 +141,6 @@
       dispatch('selectAssetCandidates', { asset });
     }
   };
-
-  const formatGroupTitle = (date: DateTime): string => {
-    const today = DateTime.now().startOf('day');
-
-    // Today
-    if (today.hasSame(date, 'day')) {
-      return 'Today';
-    }
-
-    // Yesterday
-    if (Interval.fromDateTimes(date, today).length('days') == 1) {
-      return 'Yesterday';
-    }
-
-    // Last week
-    if (Interval.fromDateTimes(date, today).length('weeks') < 1) {
-      return date.toLocaleString({ weekday: 'long' });
-    }
-
-    // This year
-    if (today.hasSame(date, 'year')) {
-      return date.toLocaleString({
-        weekday: 'short',
-        month: 'short',
-        day: 'numeric',
-      });
-    }
-
-    return date.toLocaleString({
-      weekday: 'short',
-      month: 'short',
-      day: 'numeric',
-      year: 'numeric',
-    });
-  };
 </script>
 
 <section
diff --git a/web/src/lib/components/photos-page/asset-grid.svelte b/web/src/lib/components/photos-page/asset-grid.svelte
index 7a80533163..c30a7cb3d4 100644
--- a/web/src/lib/components/photos-page/asset-grid.svelte
+++ b/web/src/lib/components/photos-page/asset-grid.svelte
@@ -2,14 +2,19 @@
   import { BucketPosition } from '$lib/models/asset-grid-state';
   import {
     assetInteractionStore,
+    assetSelectionCandidates,
+    assetSelectionStart,
     isMultiSelectStoreState,
     isViewingAssetStoreState,
     selectedAssets,
     viewingAssetStoreState,
   } from '$lib/stores/asset-interaction.store';
   import { assetGridState, assetStore, loadingBucketState } from '$lib/stores/assets.store';
+  import { locale } from '$lib/stores/preferences.store';
+  import { formatGroupTitle, splitBucketIntoDateGroups } from '$lib/utils/timeline-util';
   import type { UserResponseDto } from '@api';
   import { api, AssetCountByTimeBucketResponseDto, AssetResponseDto, TimeGroupEnum } from '@api';
+  import { DateTime } from 'luxon';
   import { onDestroy, onMount } from 'svelte';
   import AssetViewer from '../asset-viewer/asset-viewer.svelte';
   import IntersectionObserver from '../asset-viewer/intersection-observer.svelte';
@@ -144,12 +149,6 @@
     selectAssetCandidates(lastAssetMouseEvent);
   }
 
-  const getLastSelectedAsset = () => {
-    let value;
-    for (value of $selectedAssets);
-    return value;
-  };
-
   const handleSelectAssetCandidates = (e: CustomEvent) => {
     const asset = e.detail.asset;
     if (asset) {
@@ -158,18 +157,84 @@
     lastAssetMouseEvent = asset;
   };
 
+  const handleSelectAssets = async (e: CustomEvent) => {
+    const asset = e.detail.asset;
+    if (!asset) {
+      return;
+    }
+
+    const rangeSelection = $assetSelectionCandidates.size > 0;
+    const deselect = $selectedAssets.has(asset);
+
+    // Select/deselect already loaded assets
+    if (deselect) {
+      for (const candidate of $assetSelectionCandidates || []) {
+        assetInteractionStore.removeAssetFromMultiselectGroup(candidate);
+      }
+      assetInteractionStore.removeAssetFromMultiselectGroup(asset);
+    } else {
+      for (const candidate of $assetSelectionCandidates || []) {
+        assetInteractionStore.addAssetToMultiselectGroup(candidate);
+      }
+      assetInteractionStore.addAssetToMultiselectGroup(asset);
+    }
+
+    assetInteractionStore.clearAssetSelectionCandidates();
+
+    if ($assetSelectionStart && rangeSelection) {
+      let startBucketIndex = $assetGridState.loadedAssets[$assetSelectionStart.id];
+      let endBucketIndex = $assetGridState.loadedAssets[asset.id];
+
+      if (endBucketIndex < startBucketIndex) {
+        [startBucketIndex, endBucketIndex] = [endBucketIndex, startBucketIndex];
+      }
+
+      // Select/deselect assets in all intermediate buckets
+      for (let bucketIndex = startBucketIndex + 1; bucketIndex < endBucketIndex; bucketIndex++) {
+        const bucket = $assetGridState.buckets[bucketIndex];
+        await assetStore.getAssetsByBucket(bucket.bucketDate, BucketPosition.Unknown);
+        for (const asset of bucket.assets) {
+          if (deselect) {
+            assetInteractionStore.removeAssetFromMultiselectGroup(asset);
+          } else {
+            assetInteractionStore.addAssetToMultiselectGroup(asset);
+          }
+        }
+      }
+
+      // Update date group selection
+      for (let bucketIndex = startBucketIndex; bucketIndex <= endBucketIndex; bucketIndex++) {
+        const bucket = $assetGridState.buckets[bucketIndex];
+
+        // Split bucket into date groups and check each group
+        const assetsGroupByDate = splitBucketIntoDateGroups(bucket.assets, $locale);
+
+        for (const dateGroup of assetsGroupByDate) {
+          const dateGroupTitle = formatGroupTitle(DateTime.fromISO(dateGroup[0].fileCreatedAt).startOf('day'));
+          if (dateGroup.every((a) => $selectedAssets.has(a))) {
+            assetInteractionStore.addGroupToMultiselectGroup(dateGroupTitle);
+          } else {
+            assetInteractionStore.removeGroupFromMultiselectGroup(dateGroupTitle);
+          }
+        }
+      }
+    }
+
+    assetInteractionStore.setAssetSelectionStart(deselect ? null : asset);
+  };
+
   const selectAssetCandidates = (asset: AssetResponseDto) => {
     if (!shiftKeyIsDown) {
       return;
     }
 
-    const lastSelectedAsset = getLastSelectedAsset();
-    if (!lastSelectedAsset) {
+    const rangeStart = $assetSelectionStart;
+    if (!rangeStart) {
       return;
     }
 
-    let start = $assetGridState.assets.indexOf(asset);
-    let end = $assetGridState.assets.indexOf(lastSelectedAsset);
+    let start = $assetGridState.assets.indexOf(rangeStart);
+    let end = $assetGridState.assets.indexOf(asset);
 
     if (start > end) {
       [start, end] = [end, start];
@@ -230,6 +295,7 @@
                 {isAlbumSelectionMode}
                 on:shift={handleScrollTimeline}
                 on:selectAssetCandidates={handleSelectAssetCandidates}
+                on:selectAssets={handleSelectAssets}
                 assets={bucket.assets}
                 bucketDate={bucket.bucketDate}
                 bucketHeight={bucket.bucketHeight}
diff --git a/web/src/lib/stores/asset-interaction.store.ts b/web/src/lib/stores/asset-interaction.store.ts
index 0c8738c25a..1f9134f324 100644
--- a/web/src/lib/stores/asset-interaction.store.ts
+++ b/web/src/lib/stores/asset-interaction.store.ts
@@ -7,12 +7,25 @@ import { assetGridState, assetStore } from './assets.store';
 export const viewingAssetStoreState = writable<AssetResponseDto>();
 export const isViewingAssetStoreState = writable<boolean>(false);
 
-// Multi-Selection mode
+/**
+ * Multi-selection mode
+ */
 export const assetsInAlbumStoreState = writable<AssetResponseDto[]>([]);
+// Selected assets
 export const selectedAssets = writable<Set<AssetResponseDto>>(new Set());
+// Selected date groups
 export const selectedGroup = writable<Set<string>>(new Set());
+// If any asset selected
 export const isMultiSelectStoreState = derived(selectedAssets, ($selectedAssets) => $selectedAssets.size > 0);
+
+/**
+ * Range selection
+ */
+// Candidates for the range selection. This set includes only loaded assets, so it improves highlight
+// performance. From the user's perspective, range is highlighted almost immediately
 export const assetSelectionCandidates = writable<Set<AssetResponseDto>>(new Set());
+// The beginning of the selection range
+export const assetSelectionStart = writable<AssetResponseDto | null>(null);
 
 function createAssetInteractionStore() {
   let _assetGridState = new AssetGridState();
@@ -21,6 +34,7 @@ function createAssetInteractionStore() {
   let _selectedGroup: Set<string>;
   let _assetsInAlbums: AssetResponseDto[];
   let _assetSelectionCandidates: Set<AssetResponseDto>;
+  let _assetSelectionStart: AssetResponseDto | null;
 
   // Subscriber
   assetGridState.subscribe((state) => {
@@ -47,6 +61,9 @@ function createAssetInteractionStore() {
     _assetSelectionCandidates = assets;
   });
 
+  assetSelectionStart.subscribe((asset) => {
+    _assetSelectionStart = asset;
+  });
   // Methods
 
   /**
@@ -155,6 +172,11 @@ function createAssetInteractionStore() {
     selectedGroup.set(_selectedGroup);
   };
 
+  const setAssetSelectionStart = (asset: AssetResponseDto | null) => {
+    _assetSelectionStart = asset;
+    assetSelectionStart.set(_assetSelectionStart);
+  };
+
   const setAssetSelectionCandidates = (assets: AssetResponseDto[]) => {
     _assetSelectionCandidates = new Set(assets);
     assetSelectionCandidates.set(_assetSelectionCandidates);
@@ -166,15 +188,20 @@ function createAssetInteractionStore() {
   };
 
   const clearMultiselect = () => {
+    // Multi-selection
     _selectedAssets.clear();
     _selectedGroup.clear();
-    _assetSelectionCandidates.clear();
     _assetsInAlbums = [];
 
+    // Range selection
+    _assetSelectionCandidates.clear();
+    _assetSelectionStart = null;
+
     selectedAssets.set(_selectedAssets);
     selectedGroup.set(_selectedGroup);
     assetsInAlbumStoreState.set(_assetsInAlbums);
     assetSelectionCandidates.set(_assetSelectionCandidates);
+    assetSelectionStart.set(_assetSelectionStart);
   };
 
   return {
@@ -188,6 +215,7 @@ function createAssetInteractionStore() {
     removeGroupFromMultiselectGroup,
     setAssetSelectionCandidates,
     clearAssetSelectionCandidates,
+    setAssetSelectionStart,
     clearMultiselect,
   };
 }
diff --git a/web/src/lib/utils/timeline-util.ts b/web/src/lib/utils/timeline-util.ts
new file mode 100644
index 0000000000..553bfc7c88
--- /dev/null
+++ b/web/src/lib/utils/timeline-util.ts
@@ -0,0 +1,51 @@
+import type { AssetResponseDto } from '@api';
+import lodash from 'lodash-es';
+import { DateTime, Interval } from 'luxon';
+
+export const groupDateFormat: Intl.DateTimeFormatOptions = {
+  weekday: 'short',
+  month: 'short',
+  day: 'numeric',
+  year: 'numeric',
+};
+
+export function formatGroupTitle(date: DateTime): string {
+  const today = DateTime.now().startOf('day');
+
+  // Today
+  if (today.hasSame(date, 'day')) {
+    return 'Today';
+  }
+
+  // Yesterday
+  if (Interval.fromDateTimes(date, today).length('days') == 1) {
+    return 'Yesterday';
+  }
+
+  // Last week
+  if (Interval.fromDateTimes(date, today).length('weeks') < 1) {
+    return date.toLocaleString({ weekday: 'long' });
+  }
+
+  // This year
+  if (today.hasSame(date, 'year')) {
+    return date.toLocaleString({
+      weekday: 'short',
+      month: 'short',
+      day: 'numeric',
+    });
+  }
+
+  return date.toLocaleString(groupDateFormat);
+}
+
+export function splitBucketIntoDateGroups(
+  assets: AssetResponseDto[],
+  locale: string | undefined,
+): AssetResponseDto[][] {
+  return lodash
+    .chain(assets)
+    .groupBy((a) => new Date(a.fileCreatedAt).toLocaleDateString(locale, groupDateFormat))
+    .sortBy((group) => assets.indexOf(group[0]))
+    .value();
+}