diff --git a/web/components/tiptap/extensions/index.tsx b/web/components/tiptap/extensions/index.tsx
index ea5d421a6..f5dc11384 100644
--- a/web/components/tiptap/extensions/index.tsx
+++ b/web/components/tiptap/extensions/index.tsx
@@ -32,122 +32,122 @@ export const TiptapExtensions = (
   workspaceSlug: string,
   setIsSubmitting?: (isSubmitting: "submitting" | "submitted" | "saved") => void
 ) => [
-  StarterKit.configure({
-    bulletList: {
-      HTMLAttributes: {
-        class: "list-disc list-outside leading-3 -mt-2",
+    StarterKit.configure({
+      bulletList: {
+        HTMLAttributes: {
+          class: "list-disc list-outside leading-3 -mt-2",
+        },
       },
-    },
-    orderedList: {
-      HTMLAttributes: {
-        class: "list-decimal list-outside leading-3 -mt-2",
+      orderedList: {
+        HTMLAttributes: {
+          class: "list-decimal list-outside leading-3 -mt-2",
+        },
       },
-    },
-    listItem: {
-      HTMLAttributes: {
-        class: "leading-normal -mb-2",
+      listItem: {
+        HTMLAttributes: {
+          class: "leading-normal -mb-2",
+        },
       },
-    },
-    blockquote: {
-      HTMLAttributes: {
-        class: "border-l-4 border-custom-border-300",
+      blockquote: {
+        HTMLAttributes: {
+          class: "border-l-4 border-custom-border-300",
+        },
       },
-    },
-    code: {
+      code: {
+        HTMLAttributes: {
+          class:
+            "rounded-md bg-custom-primary-30 mx-1 px-1 py-1 font-mono font-medium text-custom-text-1000",
+          spellcheck: "false",
+        },
+      },
+      codeBlock: false,
+      horizontalRule: false,
+      dropcursor: {
+        color: "rgba(var(--color-text-100))",
+        width: 2,
+      },
+      gapcursor: false,
+    }),
+    CodeBlockLowlight.configure({
+      lowlight,
+    }),
+    HorizontalRule.extend({
+      addInputRules() {
+        return [
+          new InputRule({
+            find: /^(?:---|—-|___\s|\*\*\*\s)$/,
+            handler: ({ state, range, commands }) => {
+              commands.splitBlock();
+
+              const attributes = {};
+              const { tr } = state;
+              const start = range.from;
+              const end = range.to;
+              // @ts-ignore
+              tr.replaceWith(start - 1, end, this.type.create(attributes));
+            },
+          }),
+        ];
+      },
+    }).configure({
+      HTMLAttributes: {
+        class: "mb-6 border-t border-custom-border-300",
+      },
+    }),
+    Gapcursor,
+    TiptapLink.configure({
+      protocols: ["http", "https"],
+      validate: (url) => isValidHttpUrl(url),
       HTMLAttributes: {
         class:
-          "rounded-md bg-custom-primary-30 mx-1 px-1 py-1 font-mono font-medium text-custom-text-1000",
-        spellcheck: "false",
+          "text-custom-primary-300 underline underline-offset-[3px] hover:text-custom-primary-500 transition-colors cursor-pointer",
       },
-    },
-    codeBlock: false,
-    horizontalRule: false,
-    dropcursor: {
-      color: "rgba(var(--color-text-100))",
-      width: 2,
-    },
-    gapcursor: false,
-  }),
-  CodeBlockLowlight.configure({
-    lowlight,
-  }),
-  HorizontalRule.extend({
-    addInputRules() {
-      return [
-        new InputRule({
-          find: /^(?:---|—-|___\s|\*\*\*\s)$/,
-          handler: ({ state, range, commands }) => {
-            commands.splitBlock();
+    }),
+    UpdatedImage.configure({
+      HTMLAttributes: {
+        class: "rounded-lg border border-custom-border-300",
+      },
+    }),
+    Placeholder.configure({
+      placeholder: ({ node }) => {
+        if (node.type.name === "heading") {
+          return `Heading ${node.attrs.level}`;
+        }
+        if (node.type.name === "image" || node.type.name === "table") {
+          return "";
+        }
 
-            const attributes = {};
-            const { tr } = state;
-            const start = range.from;
-            const end = range.to;
-            // @ts-ignore
-            tr.replaceWith(start - 1, end, this.type.create(attributes));
-          },
-        }),
-      ];
-    },
-  }).configure({
-    HTMLAttributes: {
-      class: "mb-6 border-t border-custom-border-300",
-    },
-  }),
-  Gapcursor,
-  TiptapLink.configure({
-    protocols: ["http", "https"],
-    validate: (url) => isValidHttpUrl(url),
-    HTMLAttributes: {
-      class:
-        "text-custom-primary-300 underline underline-offset-[3px] hover:text-custom-primary-500 transition-colors cursor-pointer",
-    },
-  }),
-  UpdatedImage.configure({
-    HTMLAttributes: {
-      class: "rounded-lg border border-custom-border-300",
-    },
-  }),
-  Placeholder.configure({
-    placeholder: ({ node }) => {
-      if (node.type.name === "heading") {
-        return `Heading ${node.attrs.level}`;
-      }
-      if (node.type.name === "image" || node.type.name === "table") {
-        return "";
-      }
-
-      return "Press '/' for commands...";
-    },
-    includeChildren: true,
-  }),
-  UniqueID.configure({
-    types: ["image"],
-  }),
-  SlashCommand(workspaceSlug, setIsSubmitting),
-  TiptapUnderline,
-  TextStyle,
-  Color,
-  Highlight.configure({
-    multicolor: true,
-  }),
-  TaskList.configure({
-    HTMLAttributes: {
-      class: "not-prose pl-2",
-    },
-  }),
-  TaskItem.configure({
-    HTMLAttributes: {
-      class: "flex items-start my-4",
-    },
-    nested: true,
-  }),
-  Markdown.configure({
-    html: true,
-    transformCopiedText: true,
-  }),
-  Table,
-  TableHeader,
-  CustomTableCell,
-  TableRow,
-];
+        return "Press '/' for commands...";
+      },
+      includeChildren: true,
+    }),
+    UniqueID.configure({
+      types: ["image"],
+    }),
+    SlashCommand(workspaceSlug, setIsSubmitting),
+    TiptapUnderline,
+    TextStyle,
+    Color,
+    Highlight.configure({
+      multicolor: true,
+    }),
+    TaskList.configure({
+      HTMLAttributes: {
+        class: "not-prose pl-2",
+      },
+    }),
+    TaskItem.configure({
+      HTMLAttributes: {
+        class: "flex items-start my-4",
+      },
+      nested: true,
+    }),
+    Markdown.configure({
+      html: true,
+      transformCopiedText: true,
+    }),
+    Table,
+    TableHeader,
+    CustomTableCell,
+    TableRow,
+  ];
diff --git a/web/components/tiptap/plugins/delete-image.tsx b/web/components/tiptap/plugins/delete-image.tsx
index 568e4b748..fdf515ccc 100644
--- a/web/components/tiptap/plugins/delete-image.tsx
+++ b/web/components/tiptap/plugins/delete-image.tsx
@@ -1,43 +1,51 @@
-import { Plugin, PluginKey } from "@tiptap/pm/state";
+import { EditorState, Plugin, PluginKey, Transaction } from "@tiptap/pm/state";
 import { Node as ProseMirrorNode } from "@tiptap/pm/model";
 import fileService from "services/file.service";
 
 const deleteKey = new PluginKey("delete-image");
+const IMAGE_NODE_TYPE = "image";
 
-const TrackImageDeletionPlugin = () =>
+interface ImageNode extends ProseMirrorNode {
+  attrs: {
+    src: string;
+    id: string;
+  };
+}
+
+const TrackImageDeletionPlugin = (): Plugin =>
   new Plugin({
     key: deleteKey,
-    appendTransaction: (transactions, oldState, newState) => {
+    appendTransaction: (transactions: readonly Transaction[], oldState: EditorState, newState: EditorState) => {
+      const newImageSources = new Set();
+      newState.doc.descendants((node) => {
+        if (node.type.name === IMAGE_NODE_TYPE) {
+          newImageSources.add(node.attrs.src);
+        }
+      });
+
       transactions.forEach((transaction) => {
         if (!transaction.docChanged) return;
 
-        const removedImages: ProseMirrorNode[] = [];
+        const removedImages: ImageNode[] = [];
 
         oldState.doc.descendants((oldNode, oldPos) => {
-          if (oldNode.type.name !== "image") return;
-
+          if (oldNode.type.name !== IMAGE_NODE_TYPE) return;
           if (oldPos < 0 || oldPos > newState.doc.content.size) return;
           if (!newState.doc.resolve(oldPos).parent) return;
+
           const newNode = newState.doc.nodeAt(oldPos);
 
           // Check if the node has been deleted or replaced
-          if (!newNode || newNode.type.name !== "image") {
-            // Check if the node still exists elsewhere in the document
-            let nodeExists = false;
-            newState.doc.descendants((node) => {
-              if (node.attrs.id === oldNode.attrs.id) {
-                nodeExists = true;
-              }
-            });
-            if (!nodeExists) {
-              removedImages.push(oldNode as ProseMirrorNode);
+          if (!newNode || newNode.type.name !== IMAGE_NODE_TYPE) {
+            if (!newImageSources.has(oldNode.attrs.src)) {
+              removedImages.push(oldNode as ImageNode);
             }
           }
         });
 
-        removedImages.forEach((node) => {
+        removedImages.forEach(async (node) => {
           const src = node.attrs.src;
-          onNodeDeleted(src);
+          await onNodeDeleted(src);
         });
       });
 
@@ -47,10 +55,14 @@ const TrackImageDeletionPlugin = () =>
 
 export default TrackImageDeletionPlugin;
 
-async function onNodeDeleted(src: string) {
-  const assetUrlWithWorkspaceId = new URL(src).pathname.substring(1);
-  const resStatus = await fileService.deleteImage(assetUrlWithWorkspaceId);
-  if (resStatus === 204) {
-    console.log("Image deleted successfully");
+async function onNodeDeleted(src: string): Promise<void> {
+  try {
+    const assetUrlWithWorkspaceId = new URL(src).pathname.substring(1);
+    const resStatus = await fileService.deleteImage(assetUrlWithWorkspaceId);
+    if (resStatus === 204) {
+      console.log("Image deleted successfully");
+    }
+  } catch (error) {
+    console.error("Error deleting image: ", error);
   }
 }
diff --git a/web/components/tiptap/plugins/upload-image.tsx b/web/components/tiptap/plugins/upload-image.tsx
index 499a00455..bc0acdc54 100644
--- a/web/components/tiptap/plugins/upload-image.tsx
+++ b/web/components/tiptap/plugins/upload-image.tsx
@@ -1,4 +1,3 @@
-// @ts-nocheck
 import { EditorState, Plugin, PluginKey } from "@tiptap/pm/state";
 import { Decoration, DecorationSet, EditorView } from "@tiptap/pm/view";
 import fileService from "services/file.service";