Question: My application needs to save multiple versions of an uploaded Image. One high quality image and another one just for thumbnails use (low quality). Currently this is working most of the time but sometimes the save method simply fails and all of my Thumbnail images are getting deleted, especially then if I use the remove_cover checkbox at my form  raise ValueError("The '%s' attribute has no file associated with it." % self.field.name) app | ValueError: The 'postcover_tn' attribute has no file associated with it.  -> See full trace here: https://pastebin.com/hgieMGet models.py class Post(models.Model): id = models.UUIDField(primary_key=True, default=uuid.uuid4, editable=False) author = models.ForeignKey(User, on_delete=models.CASCADE) title = models.CharField() content = models.TextField(blank=False) postcover = models.ImageField( verbose_name="Post Cover", blank=True, null=True, upload_to=image_uploads, ) postcover_tn = models.ImageField( verbose_name="Post Cover Thumbnail", blank=True, null=True, upload_to=image_uploads, ) published_date = models.DateTimeField(auto_now_add=True, null=True) def save(self, *args, **kwargs): super(Post, self).save(*args, **kwargs) if self.postcover: if not (self.postcover_tn and os.path.exists(self.postcover_tn.path)): image = Image.open(self.postcover) outputIoStream = BytesIO() baseheight = 500 hpercent = baseheight / image.size[1] wsize = int(image.size[0] * hpercent) imageTemproaryResized = image.resize((wsize, baseheight)) imageTemproaryResized.save(outputIoStream, format='PNG') outputIoStream.seek(0) self.postcover = InMemoryUploadedFile(outputIoStream, 'ImageField', "%s.png" % self.postcover.name.split('.')[0], 'image/png', sys.getsizeof(outputIoStream), None) image = Image.open(self.postcover) outputIoStream = BytesIO() baseheight = 175 hpercent = baseheight / image.size[1] wsize = int(image.size[0] * hpercent) imageTemproaryResized = image.resize((wsize, baseheight)) imageTemproaryResized.save(outputIoStream, format='PNG') outputIoStream.seek(0) self.postcover_tn = InMemoryUploadedFile(outputIoStream, 'ImageField', "%s.png" % self.postcover.name.split('.')[0], 'image/png', sys.getsizeof(outputIoStream), None) elif self.postcover_tn: self.postcover_tn.delete() super(Post, self).save(*args, **kwargs)  It also seems that I'm not able to properly resolve:  self.postcover_tn.delete() -> Unresolved attribute reference 'delete' for class 'InMemoryUploadedFile' self.postcover_tn.path -> Unresolved attribute reference 'path' for class 'InMemoryUploadedFile'  forms.py: def save(self, commit=True): instance = super(PostForm, self).save(commit=False) if self.cleaned_data.get('remove_cover'): try: os.unlink(instance.postcover.path) except OSError: pass instance.postcover = None if commit: instance.save() return instance 

Answer: maybe if we look at the problem from another angle, we could solve it otherwise, out of the box. signals are very handy when it comes to handle images (add, update and delete) and below how i managed to solve your issue: in models.py: # from django.template.defaultfilters import slugify class Post(models.Model): id = models.UUIDField(primary_key=True, default=uuid.uuid4, editable=False) author = models.ForeignKey(User, on_delete=models.CASCADE) title = models.CharField() # slug = models.SlugField('slug', max_length=255, # unique=True, null=True, blank=True, # help_text='If blank, the slug will be generated automatically from the given title.' # ) content = models.TextField(blank=False) # ------------------------------------------------------------------------------------ # rename images with the current post id/pk (which is UUID) and keep the extension # for cover thumbnail we append "_thumbnail" to the name # e.g: # img/posts/77b122a3d241461b80c51adc41d719fb.jpg # img/posts/77b122a3d241461b80c51adc41d719fb_thumbnail.jpg def upload_cover(instance, filename): ext = filename.split('.')[-1] filename = '{}.{}'.format(instance.id, ext) path = 'img/posts/' return '{}{}'.format(path, filename) postcover = models.ImageField('Post Cover', upload_to=upload_cover, # callback function null=True, blank=True, help_text=_('Upload Post Cover.') ) def upload_thumbnail(instance, filename): ext = filename.split('.')[-1] filename = '{}_thumbnail.{}'.format(instance.id, ext) path = 'img/posts/' return '{}{}'.format(path, filename) postcover_tn = models.ImageField('Post Cover Thumbnail', upload_to=upload_thumbnail, # callback function null=True, blank=True, help_text=_('Upload Post Cover Thumbnail.') ) # ------------------------------------------------------------------------------------ published_date = models.DateTimeField(auto_now_add=True, null=True) def save(self, *args, **kwargs): # i moved the logic to signals # if not self.slug: # self.slug = slugify(self.title) super(Post, self).save(*args, **kwargs)  create new file and rename it signals.py (near to models.py): import io import sys from PIL import Image from django.core.files.uploadedfile import InMemoryUploadedFile from django.dispatch import receiver from django.db.models.signals import pre_save, pre_delete from .models import Post # DRY def image_resized(image, h): name = image.name _image = Image.open(image) content_type = Image.MIME[_image.format] r = h / _image.size[1] # ratio w = int(_image.size[0] * r) imageTemproaryResized = _image.resize((w, h)) file = io.BytesIO() imageTemproaryResized.save(file, _image.format) file.seek(0) size = sys.getsizeof(file) return file, name, content_type, size @receiver(pre_save, sender=Post, dispatch_uid='post.save_image') def save_image(sender, instance, **kwargs): # add image (cover | thumbnail) if instance._state.adding: # postcover file, name, content_type, size = image_resized(instance.postcover, 500) instance.postcover = InMemoryUploadedFile(file, 'ImageField', name, content_type, size, None) # postcover_tn file, name, content_type, size = image_resized(instance.postcover_tn, 175) instance.postcover_tn = InMemoryUploadedFile(file, 'ImageField', name, content_type, size, None) # update image (cover | thumbnail) if not instance._state.adding: # we have 2 cases: # - replace old with new # - delete old (when 'clear' checkbox is checked) # postcover old = sender.objects.get(pk=instance.pk).postcover new = instance.postcover if (old and not new) or (old and new and old.url != new.url): old.delete(save=False) # postcover_tn old = sender.objects.get(pk=instance.pk).postcover_tn new = instance.postcover_tn if (old and not new) or (old and new and old.url != new.url): old.delete(save=False) @receiver(pre_delete, sender=Post, dispatch_uid='post.delete_image') def delete_image(sender, instance, **kwargs): s = sender.objects.get(pk=instance.pk) if (not s.postcover or s.postcover is not None) and (not s.postcover_tn or s.postcover_tn is not None): s.postcover.delete(False) s.postcover_tn.delete(False)  in apps.py: we need to register signals in apps.py since we use decorators @receiver: from django.apps import AppConfig from django.utils.translation import ugettext_lazy as _ class BlogConfig(AppConfig): # change to the name of your app name = 'blog' # and here verbose_name = _('Blog Entries') def ready(self): from . import signals  and this is the first screen shot of post admin area  since the thumbnail is generated from post cover, as UI/UX good practices there's no need to show a second input file for post cover thumbnail (i kept the second image field read only in admin.py). below is the second screenshot after i uploaded the image PS: the screenshot is taken from another app that i'm working on, so there's little changes, in your case you should see  Post Cover instead Featured Image Currently: img/posts/8b0be417db564c53ad06cb493029e2ca.jpg (see upload_cover() in models.py) instead  Currently: img/blog/posts/featured/8b0be417db564c53ad06cb493029e2ca.jpg   in admin.py # "img/posts/default.jpg" and "img/posts/default_thumbnail.jpg" are placeholders # grab to 2 image placeholders from internet and put them under "/static" folder def get_post_cover(obj): src = obj.postcover.url if obj.postcover and \ hasattr(obj.postcover, 'url') else os.path.join( settings.STATIC_URL, 'img/posts/default.jpg') return mark_safe('<img src="{}" height="500" style="border:1px solid #ccc">'.format(src)) get_post_cover.short_description = '' get_post_cover.allow_tags = True def get_post_cover_thumbnail(obj): src = obj.postcover_tn.url if obj.postcover_tn and \ hasattr(obj.postcover_tn, 'url') else os.path.join( settings.STATIC_URL, 'img/posts/default_thumbnail.jpg') return mark_safe('<img src="{}" height="175" style="border:1px solid #ccc">'.format(src)) get_post_cover_thumbnail.short_description = '' get_post_cover_thumbnail.allow_tags = True class PostAdmin(admin.ModelAdmin): list_display = ('title', .. ) fields = ( 'author', 'title', 'content', get_post_cover, get_post_cover_thumbnail, 'postcover', ) readonly_fields = (get_post_cover, get_post_cover_thumbnail) [..]  and finally you don't need any delete logic in save() function in forms.py