diff --git a/lib/Artwork.php b/lib/Artwork.php
index 3aecb008..164210a6 100644
--- a/lib/Artwork.php
+++ b/lib/Artwork.php
@@ -508,6 +508,13 @@ final class Artwork{
 				$error->Add(new Exceptions\InvalidImageUploadException('An image is required.'));
 			}
 			else{
+				try{
+					$this->MimeType = Enums\ImageMimeType::FromFile($imagePath) ?? throw new Exceptions\InvalidMimeTypeException();
+				}
+				catch(Exceptions\InvalidMimeTypeException $ex){
+					$error->Add($ex);
+				}
+
 				if(!is_writable(WEB_ROOT . COVER_ART_UPLOAD_PATH)){
 					$error->Add(new Exceptions\InvalidImageUploadException('Upload path not writable.'));
 				}
@@ -525,10 +532,6 @@ final class Artwork{
 			}
 		}
 
-		if(!isset($this->MimeType)){
-			$error->Add(new Exceptions\InvalidMimeTypeException());
-		}
-
 		if($error->HasExceptions){
 			throw $error;
 		}
@@ -681,8 +684,6 @@ final class Artwork{
 	 * @throws Exceptions\InvalidImageUploadException
 	 */
 	public function Create(?string $imagePath = null): void{
-		$this->MimeType = Enums\ImageMimeType::FromFile($imagePath) ?? throw new Exceptions\InvalidImageUploadException();
-
 		$this->Validate($imagePath, true);
 
 		$this->Created = NOW;
@@ -750,8 +751,6 @@ final class Artwork{
 		unset($this->_UrlName);
 
 		if($imagePath !== null){
-			$this->MimeType = Enums\ImageMimeType::FromFile($imagePath) ?? throw new Exceptions\InvalidImageUploadException();
-
 			// Manually set the updated timestamp, because if we only update the image and nothing else, the row's updated timestamp won't change automatically.
 			$this->Updated = NOW;
 			unset($this->_ImageUrl);
diff --git a/lib/Exceptions/ValidationException.php b/lib/Exceptions/ValidationException.php
index 3dcb2c6f..2746de32 100644
--- a/lib/Exceptions/ValidationException.php
+++ b/lib/Exceptions/ValidationException.php
@@ -45,4 +45,16 @@ class ValidationException extends AppException{
 
 		return false;
 	}
+
+	public function Remove(string $exception): void{
+		$newExceptions = [];
+
+		foreach($this->Exceptions as $childException){
+			if(!is_a($childException, $exception)){
+				$newExceptions[] = $childException;
+			}
+		}
+
+		$this->Exceptions = $newExceptions;
+	}
 }
diff --git a/www/artworks/post.php b/www/artworks/post.php
index 38412cbc..aad357f2 100644
--- a/www/artworks/post.php
+++ b/www/artworks/post.php
@@ -7,10 +7,6 @@ try{
 	$exceptionRedirectUrl = '/artworks/new';
 	$artwork = new Artwork();
 
-	if(HttpInput::IsRequestTooLarge()){
-		throw new Exceptions\InvalidRequestException('File upload too large.');
-	}
-
 	if(Session::$User === null){
 		throw new Exceptions\LoginRequiredException();
 	}
@@ -164,6 +160,12 @@ catch(Exceptions\InvalidArtworkException | Exceptions\InvalidArtworkTagException
 		$ex = new Exceptions\InvalidImageUploadException();
 	}
 
+	// If the `Artwork` reports that no image is uploaded, check to see if the image upload was too large. If so, show the user a clearer error message.
+	if($ex instanceof Exceptions\InvalidArtworkException && $ex->Has(Exceptions\InvalidImageUploadException::class) && HttpInput::IsRequestTooLarge()){
+		$ex->Remove(Exceptions\InvalidImageUploadException::class);
+		$ex->Add(new Exceptions\InvalidRequestException('File upload too large.'));
+	}
+
 	$_SESSION['artwork'] = $artwork;
 	$_SESSION['exception'] = $ex;