diff --git a/frontend/pages/warrens/files.vue b/frontend/pages/warrens/files.vue
index 52124ba..0aabfdc 100644
--- a/frontend/pages/warrens/files.vue
+++ b/frontend/pages/warrens/files.vue
@@ -79,13 +79,79 @@ function onDrop(files: File[] | null, e: DragEvent) {
     }
 }
 
+/**
+ * Returns whether the event was a selection event (so further execution can be stopped)
+ */
+function handleEntrySelectionClick(
+    selectedEntry: DirectoryEntry,
+    event: MouseEvent
+): boolean {
+    if (!event.ctrlKey && !event.shiftKey) {
+        return false;
+    }
+
+    if (warrenStore.current == null || warrenStore.current.dir == null) {
+        return true;
+    }
+
+    if (event.ctrlKey || (event.shiftKey && warrenStore.selection.size === 0)) {
+        if (
+            warrenStore.toggleSelection(selectedEntry) ||
+            warrenStore.selectionRangeAnchor == null
+        ) {
+            warrenStore.setSelectedRangeAnchor(selectedEntry);
+        }
+        return true;
+    }
+
+    if (!event.shiftKey) {
+        return false;
+    }
+
+    const anchor = warrenStore.selectionRangeAnchor;
+
+    if (anchor == null) {
+        return true;
+    }
+
+    const entries = warrenStore.current.dir.entries.toSorted((a, b) =>
+        a.name.localeCompare(b.name)
+    );
+    const anchorIndex = entries.findIndex(
+        (entry) => entry.name === anchor.name
+    );
+
+    const clickedIndex = entries.findIndex(
+        (e) => e.name === selectedEntry.name
+    );
+
+    // NOTE: This has to change if there are ever multiple sorting orders
+
+    const targetSelection = [];
+
+    if (clickedIndex > anchorIndex) {
+        for (let i = anchorIndex; i <= clickedIndex; i++) {
+            targetSelection.push(entries[i]);
+        }
+    } else {
+        for (let i = clickedIndex; i <= anchorIndex; i++) {
+            targetSelection.push(entries[i]);
+        }
+    }
+
+    warrenStore.setSelection(targetSelection);
+
+    return true;
+}
+
 async function onEntryClicked(entry: DirectoryEntry, event: MouseEvent) {
+    event.stopPropagation();
+
     if (warrenStore.loading || warrenStore.current == null) {
         return;
     }
 
-    if (event.ctrlKey) {
-        warrenStore.toggleSelection(entry);
+    if (handleEntrySelectionClick(entry, event)) {
         return;
     }
 
@@ -156,10 +222,14 @@ async function onEntryDelete(entry: DirectoryEntry, force: boolean) {
 function onBack() {
     warrenStore.backCurrentPath();
 }
+
+function onParentClick() {
+    warrenStore.clearSelection();
+}
 </script>
 
 <template>
-    <div ref="dropZoneRef" class="grow">
+    <div ref="dropZoneRef" class="grow" @click="onParentClick">
         <DirectoryListContextMenu class="w-full grow">
             <DirectoryList
                 v-if="
diff --git a/frontend/stores/index.ts b/frontend/stores/index.ts
index ad847bb..6f80d31 100644
--- a/frontend/stores/index.ts
+++ b/frontend/stores/index.ts
@@ -18,6 +18,7 @@ export const useWarrenStore = defineStore('warrens', {
             } | null;
         } | null,
         selection: new Set() as Set<DirectoryEntry>,
+        selectionRangeAnchor: null as DirectoryEntry | null,
         loading: false,
     }),
     actions: {
@@ -86,19 +87,33 @@ export const useWarrenStore = defineStore('warrens', {
         addToSelection(entry: DirectoryEntry) {
             this.selection.add(entry);
         },
+        setSelection(entries: DirectoryEntry[]) {
+            this.selection = new Set(entries);
+            if (
+                this.selectionRangeAnchor != null &&
+                !this.selection.has(this.selectionRangeAnchor)
+            ) {
+                this.selectionRangeAnchor = null;
+            }
+        },
         addMultipleToSelection(entries: DirectoryEntry[]) {
             for (const entry of entries) {
                 this.selection.add(entry);
             }
         },
+        setSelectedRangeAnchor(entry: DirectoryEntry) {
+            this.selectionRangeAnchor = entry;
+        },
         removeFromSelection(entry: DirectoryEntry): boolean {
             return this.selection.delete(entry);
         },
-        toggleSelection(entry: DirectoryEntry) {
+        toggleSelection(entry: DirectoryEntry): boolean {
             if (this.selection.has(entry)) {
                 this.removeFromSelection(entry);
+                return false;
             } else {
                 this.addToSelection(entry);
+                return true;
             }
         },
         isSelected(entry: DirectoryEntry): boolean {
@@ -110,6 +125,7 @@ export const useWarrenStore = defineStore('warrens', {
         },
         clearSelection() {
             this.selection.clear();
+            this.selectionRangeAnchor = null;
         },
     },
 });