diff --git a/packages/ketcher-core/src/application/editor/operations/rasterImage/rasterImageUpsertDelete.ts b/packages/ketcher-core/src/application/editor/operations/rasterImage/rasterImageUpsertDelete.ts
index f6bc3f9c0c..2791a43992 100644
--- a/packages/ketcher-core/src/application/editor/operations/rasterImage/rasterImageUpsertDelete.ts
+++ b/packages/ketcher-core/src/application/editor/operations/rasterImage/rasterImageUpsertDelete.ts
@@ -58,6 +58,7 @@ export class RasterImageDelete extends BaseOperation {
       return;
     }
 
+    this.rasterImage = reRasterImage.rasterImage.clone();
     reStruct.clearVisel(reRasterImage.visel);
     reRasterImage.remove();
     reStruct.markItemRemoved();
diff --git a/packages/ketcher-core/src/domain/serializers/ket/schema.json b/packages/ketcher-core/src/domain/serializers/ket/schema.json
index 47b9513661..bf36f4f5a2 100644
--- a/packages/ketcher-core/src/domain/serializers/ket/schema.json
+++ b/packages/ketcher-core/src/domain/serializers/ket/schema.json
@@ -70,6 +70,11 @@
         }
       }
     },
+    "imageFile": {
+      "type": "string",
+      "pattern": "^data:image/(png|jpeg|bmp|webp|x-icon|svg\\+xml);base64,",
+      "minLength": 160
+    },
     "header": {
       "type": "object",
       "properties": {
@@ -808,11 +813,21 @@
           "required": ["bitmap", "halfSize"],
           "properties": {
             "bitmap": {
-              "type": "string",
-              "minLength": 1
+              "$ref": "#/definitions/imageFile"
             },
             "halfSize": {
-              "$ref": "#/definitions/2dCoordinates"
+              "type": "object",
+              "required": ["x", "y"],
+              "properties": {
+                "x": {
+                  "type": "number",
+                  "exclusiveMinimum": 0
+                },
+                "y": {
+                  "type": "number",
+                  "exclusiveMinimum": 0
+                }
+              }
             }
           }
         }
diff --git a/packages/ketcher-react/src/script/editor/shared/closest.ts b/packages/ketcher-react/src/script/editor/shared/closest.ts
index 9d5e76ec9f..894651da52 100644
--- a/packages/ketcher-react/src/script/editor/shared/closest.ts
+++ b/packages/ketcher-react/src/script/editor/shared/closest.ts
@@ -710,6 +710,9 @@ function findClosestRasterImage(
       const distanceToPoint =
         item.rasterImage.calculateDistanceToPoint(cursorPosition);
       if (distanceToPoint < SELECTION_DISTANCE_COEFFICIENT) {
+        if (acc && acc.dist < distanceToPoint) {
+          return acc;
+        }
         return { id, dist: distanceToPoint };
       }
       return acc;
diff --git a/packages/ketcher-react/src/script/editor/tool/rasterImage.ts b/packages/ketcher-react/src/script/editor/tool/rasterImage.ts
index 94bc49a8c3..66566f4f8a 100644
--- a/packages/ketcher-react/src/script/editor/tool/rasterImage.ts
+++ b/packages/ketcher-react/src/script/editor/tool/rasterImage.ts
@@ -4,9 +4,14 @@ import {
   Vec2,
   fromRasterImageCreation,
   Editor,
+  KetcherLogger,
 } from 'ketcher-core';
 import { Tool } from './Tool';
 
+const TAG = 'tool/rasterImage.ts';
+const allowList = /image\/(png|jpeg|bmp|webp|x-icon|svg\+xml)/;
+const MIN_DIMENSION_SIZE = 16;
+
 export class RasterImageTool implements Tool {
   static readonly INPUT_ID = 'image-upload';
   private element: HTMLInputElement;
@@ -30,16 +35,43 @@ export class RasterImageTool implements Tool {
   }
 
   onFileUpload(clickPosition: Vec2): void {
+    const errorHandler = this.editor.errorHandler;
     this.element.onchange = null;
     if (this.element.files && this.element.files[0]) {
+      const file = this.element.files[0];
       const image = new Image();
       const reader = new FileReader();
 
+      if (!file.type.match(allowList)) {
+        const errorMesssage = `Wrong mime type: ${file.type}`;
+        KetcherLogger.error(`${TAG}:onFileUpload`, errorMesssage);
+        if (errorHandler) {
+          errorHandler(errorMesssage);
+        }
+
+        this.resetElementValue();
+        return;
+      }
+
       reader.addEventListener('load', () => {
         image.src = reader.result as string;
       });
 
       image.onload = () => {
+        this.resetElementValue();
+        if (
+          image.width < MIN_DIMENSION_SIZE ||
+          image.height < MIN_DIMENSION_SIZE
+        ) {
+          const errorMessage =
+            'Image should have be at least 16px wide and 16px tall';
+          KetcherLogger.error(`${TAG}:onLoad`, errorMessage);
+          if (errorHandler) {
+            errorHandler(errorMessage);
+          }
+          return;
+        }
+
         const halfSize = Scale.canvasToModel(
           new Vec2(image.width / 2, image.height / 2),
           this.editor.render.options,
@@ -53,7 +85,15 @@ export class RasterImageTool implements Tool {
             halfSize,
           ),
         );
+      };
+
+      image.onerror = (e) => {
         this.resetElementValue();
+        const errorMessage = 'Cannot load image';
+        KetcherLogger.error(`${TAG}:onerror`, errorMessage, e);
+        if (errorHandler) {
+          errorHandler(errorMessage);
+        }
       };
 
       reader.readAsDataURL(this.element.files[0]);