diff --git a/invokeai/frontend/web/src/features/gallery/components/ImageContextMenu/SingleSelectionMenuItems.tsx b/invokeai/frontend/web/src/features/gallery/components/ImageContextMenu/SingleSelectionMenuItems.tsx
index b24146c798..e97affb322 100644
--- a/invokeai/frontend/web/src/features/gallery/components/ImageContextMenu/SingleSelectionMenuItems.tsx
+++ b/invokeai/frontend/web/src/features/gallery/components/ImageContextMenu/SingleSelectionMenuItems.tsx
@@ -36,7 +36,7 @@ import {
 import { ImageDTO } from 'services/api/types';
 import { useDebounce } from 'use-debounce';
 import { sentImageToCanvas, sentImageToImg2Img } from '../../store/actions';
-import { BsPinAngle, BsPinAngleFill } from 'react-icons/bs';
+import { BsBookmarkStar, BsFillBookmarkStarFill } from 'react-icons/bs';
 
 type SingleSelectionMenuItemsProps = {
   imageDTO: ImageDTO;
@@ -211,11 +211,14 @@ const SingleSelectionMenuItems = (props: SingleSelectionMenuItemsProps) => {
         Change Board
       </MenuItem>
       {imageDTO.pinned ? (
-        <MenuItem icon={<BsPinAngle />} onClickCapture={handleUnpinImage}>
+        <MenuItem icon={<BsBookmarkStar />} onClickCapture={handleUnpinImage}>
           Unpin Image
         </MenuItem>
       ) : (
-        <MenuItem icon={<BsPinAngleFill />} onClickCapture={handlePinImage}>
+        <MenuItem
+          icon={<BsFillBookmarkStarFill />}
+          onClickCapture={handlePinImage}
+        >
           Pin Image
         </MenuItem>
       )}
diff --git a/invokeai/frontend/web/src/features/gallery/components/ImageGrid/GalleryImage.tsx b/invokeai/frontend/web/src/features/gallery/components/ImageGrid/GalleryImage.tsx
index 97f8199aed..aba5181882 100644
--- a/invokeai/frontend/web/src/features/gallery/components/ImageGrid/GalleryImage.tsx
+++ b/invokeai/frontend/web/src/features/gallery/components/ImageGrid/GalleryImage.tsx
@@ -2,16 +2,19 @@ import { Box, Flex } from '@chakra-ui/react';
 import { useAppDispatch, useAppSelector } from 'app/store/storeHooks';
 import IAIDndImage from 'common/components/IAIDndImage';
 import IAIFillSkeleton from 'common/components/IAIFillSkeleton';
-import { useMultiselect } from 'features/gallery/hooks/useMultiselect.ts';
 import { imagesToDeleteSelected } from 'features/deleteImageModal/store/slice';
-import { MouseEvent, memo, useCallback, useMemo } from 'react';
-import { FaTrash } from 'react-icons/fa';
-import { useGetImageDTOQuery } from 'services/api/endpoints/images';
 import {
   ImageDTOsDraggableData,
   ImageDraggableData,
   TypesafeDraggableData,
 } from 'features/dnd/types';
+import { useMultiselect } from 'features/gallery/hooks/useMultiselect.ts';
+import { MouseEvent, memo, useCallback, useMemo } from 'react';
+import { BsBookmarkStar, BsFillBookmarkStarFill } from 'react-icons/bs';
+import {
+  useChangeImagePinnedMutation,
+  useGetImageDTOQuery,
+} from 'services/api/endpoints/images';
 
 interface HoverableImageProps {
   imageName: string;
@@ -59,6 +62,14 @@ const GalleryImage = (props: HoverableImageProps) => {
     }
   }, [imageDTO, selection, selectionCount]);
 
+  const [togglePin] = useChangeImagePinnedMutation();
+
+  const togglePinnedState = useCallback(() => {
+    if (imageDTO) {
+      togglePin({ imageDTO, pinned: !imageDTO.pinned });
+    }
+  }, [togglePin, imageDTO]);
+
   if (!imageDTO) {
     return <IAIFillSkeleton />;
   }
@@ -80,15 +91,17 @@ const GalleryImage = (props: HoverableImageProps) => {
           draggableData={draggableData}
           isSelected={isSelected}
           minSize={0}
-          onClickReset={handleDelete}
+          onClickReset={togglePinnedState}
           imageSx={{ w: 'full', h: 'full' }}
           isDropDisabled={true}
           isUploadDisabled={true}
           thumbnail={true}
           withHoverOverlay
-          resetIcon={<FaTrash />}
-          resetTooltip="Delete image"
-          withResetIcon={shouldShowDeleteButton} // removed bc it's too easy to accidentally delete images
+          resetIcon={
+            imageDTO.pinned ? <BsFillBookmarkStarFill /> : <BsBookmarkStar />
+          }
+          resetTooltip="Pin image"
+          withResetIcon={true}
         />
       </Flex>
     </Box>
diff --git a/invokeai/frontend/web/src/services/api/endpoints/images.ts b/invokeai/frontend/web/src/services/api/endpoints/images.ts
index 9320e7a137..ef99d735c2 100644
--- a/invokeai/frontend/web/src/services/api/endpoints/images.ts
+++ b/invokeai/frontend/web/src/services/api/endpoints/images.ts
@@ -399,15 +399,18 @@ export const imagesApi = api.injectEndpoints({
         method: 'PATCH',
         body: { pinned },
       }),
-      invalidatesTags: (result, error, { imageDTO }) => [
-        {
-          type: 'ImageList',
-          id: getListImagesUrl({
-            board_id: imageDTO.board_id,
-            categories: IMAGE_CATEGORIES,
-          }),
-        },
-      ],
+      invalidatesTags: (result, error, { imageDTO }) => {
+        const categories = getCategories(imageDTO);
+        return [
+          {
+            type: 'ImageList',
+            id: getListImagesUrl({
+              board_id: imageDTO.board_id,
+              categories,
+            }),
+          },
+        ]
+      },
       async onQueryStarted(
         { imageDTO, pinned },
         { dispatch, queryFulfilled, getState }
@@ -465,27 +468,14 @@ export const imagesApi = api.injectEndpoints({
         const isCacheFullyPopulated =
           currentCache.data && currentCache.data.ids.length >= (total ?? 0);
 
-        const isInDateRangeForPinnedState = getIsImageInDateRange(
+        const isInDateRange = getIsImageInDateRange(
           currentCache.data,
           updatedImage
         );
 
-        if (!isInDateRangeForPinnedState) {
-          // if newly pinned or unpinned image is not in date range for its new state, remove from cache
-          patches.push(
-            dispatch(
-              imagesApi.util.updateQueryData(
-                'listImages',
-                queryArgs,
-                (draft) => {
-                  imagesAdapter.removeOne(draft, updatedImage.image_name);
-                }
-              )
-            )
-          );
-        }
+        // should we remove images from cache if _not_ in date range? ie you are showing 100 of 101 pinned images and you unpin one. technically it should disappear from list.
 
-        if (isCacheFullyPopulated || isInDateRangeForPinnedState) {
+        if (isCacheFullyPopulated || isInDateRange) {
           // *upsert* to $cache
           patches.push(
             dispatch(
diff --git a/invokeai/frontend/web/src/services/api/util.ts b/invokeai/frontend/web/src/services/api/util.ts
index 10c4557eec..a97e96f312 100644
--- a/invokeai/frontend/web/src/services/api/util.ts
+++ b/invokeai/frontend/web/src/services/api/util.ts
@@ -21,21 +21,35 @@ export const getIsImageInDateRange = (
     return true;
   }
 
-  const cacheImageDTOSForPinnedState = totalCachedImageDtos.filter((image) => image.pinned === imageDTO.pinned);
+  const cachedPinnedImages = [];
+  const cachedUnpinnedImages = [];
 
-  if (cacheImageDTOSForPinnedState.length > 1) {
-    // Images are sorted by `pinned` DESC and then `created_at` DESC
-    // check if the image is newer than the oldest image in the cache for either the pinned group or unpinned group
+  for (let index = 0; index < totalCachedImageDtos.length; index++) {
+    const image = totalCachedImageDtos[index];
+    if (image?.pinned) cachedPinnedImages.push(image)
+    if (!image?.pinned) cachedUnpinnedImages.push(image)
+  }
+
+  const lastPinnedImage = cachedPinnedImages[cachedPinnedImages.length - 1];
+  const lastUnpinnedImage = cachedUnpinnedImages[cachedUnpinnedImages.length - 1];
+
+  if (!lastPinnedImage || !lastUnpinnedImage) {
+    // satisfy TS gods, we already confirmed the array has more than one image
+    return false;
+  }
+
+  if (imageDTO.pinned) {
+    // if pinning or already pinned, want to look in list of pinned images 
     const createdDate = new Date(imageDTO.created_at);
-    const oldestImage = cacheImageDTOSForPinnedState[cacheImageDTOSForPinnedState.length - 1];
-    if (!oldestImage) {
-      // satisfy TS gods, we already confirmed the array has more than one image
-      return false;
-    }
-    const oldestDate = new Date(oldestImage.created_at);
+    const oldestDate = new Date(lastPinnedImage.created_at);
+    return createdDate >= oldestDate;
+  } else {
+    // if unpinning or already unpinned, want to look in list of unpinned images 
+    const createdDate = new Date(imageDTO.created_at);
+    const oldestDate = new Date(lastUnpinnedImage.created_at);
     return createdDate >= oldestDate;
   }
-  return false;
+
 };
 
 export const getCategories = (imageDTO: ImageDTO) => {