diff --git a/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_image_payload.rs b/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_image_payload.rs
index 9ed3bfa2f1..a0b3b3ee63 100644
--- a/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_image_payload.rs
+++ b/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_image_payload.rs
@@ -1,12 +1,11 @@
+use crate::http_server::common_responses::advanced_common_web_error::AdvancedCommonWebError;
 use crate::http_server::endpoints::webhooks::process_success::resolve_file_metadata::resolve_file_metadata;
 use crate::state::server_state::ServerState;
 use crate::util::http_download_url_to_bytes::http_download_url_to_bytes;
-use anyhow::anyhow;
 use bucket_paths::legacy::typified_paths::public::media_files::bucket_file_path::MediaFileBucketPath;
 use enums::by_table::media_files::media_file_class::MediaFileClass;
 use enums::by_table::media_files::media_file_origin_category::MediaFileOriginCategory;
 use enums::by_table::media_files::media_file_type::MediaFileType;
-use errors::AnyhowResult;
 use fal_client::webhook_api::hydrated::hydrated_webhook_contents::ImageData;
 use hashing::sha256::sha256_hash_bytes::sha256_hash_bytes;
 use images::encoding::webp_bytes_to_png_bytes::webp_bytes_to_png_bytes;
@@ -23,15 +22,21 @@ pub async fn process_image_payload(
   image_data: &ImageData,
   job: &FalJobDetails,
   server_state: &ServerState,
-) -> AnyhowResult<MediaFileToken> {
+) -> Result<MediaFileToken, AdvancedCommonWebError> {
   let image_url = image_data.url
       .as_deref()
-      .ok_or_else(|| anyhow!("no `url` in image payload"))?;
+      .ok_or_else(|| {
+        warn!("No `url` in image payload");
+        AdvancedCommonWebError::server_error_with_message("no `url` in image payload")
+      })?;
 
   // Download with a retry if the first attempt returns suspiciously few bytes.
   let mut file_bytes = http_download_url_to_bytes(image_url)
       .await
-      .map_err(|e| anyhow!("Failed to download image: {:?}", e))?;
+      .map_err(|err| {
+        warn!("Failed to download image from {}: {:?}", image_url, err);
+        AdvancedCommonWebError::from_anyhow_error(err)
+      })?;
 
   if file_bytes.len() <= 10 {
     warn!(
@@ -41,16 +46,24 @@ pub async fn process_image_payload(
     );
     file_bytes = http_download_url_to_bytes(image_url)
         .await
-        .map_err(|e| anyhow!("Failed to download image on retry: {:?}", e))?;
+        .map_err(|err| {
+          warn!("Failed to download image on retry from {}: {:?}", image_url, err);
+          AdvancedCommonWebError::from_anyhow_error(err)
+        })?;
   }
 
   // Resolve mime type: magic bytes first, fal content_type as fallback.
   let metadata = resolve_file_metadata(&file_bytes, image_data.content_type.as_deref())
-      .ok_or_else(|| anyhow!(
-        "Could not determine file type for image (bytes: {}, fal content_type: {:?})",
-        file_bytes.len(),
-        image_data.content_type,
-      ))?;
+      .ok_or_else(|| {
+        warn!(
+          "Could not determine file type for image (bytes: {}, fal content_type: {:?})",
+          file_bytes.len(),
+          image_data.content_type,
+        );
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Could not determine file type for image (bytes: {}, fal content_type: {:?})",
+            file_bytes.len(), image_data.content_type))
+      })?;
 
   info!("File type: {}, extension: {:?}, source: {:?}",
     metadata.mime_type, metadata.file_extension, metadata.source);
@@ -59,10 +72,18 @@ pub async fn process_image_payload(
     FileExtension::Webp => {
       info!("Artcraft can't handle WebP images yet; converting to PNG...");
 
-      let converted = webp_bytes_to_png_bytes(&file_bytes)?;
+      let converted = webp_bytes_to_png_bytes(&file_bytes)
+          .map_err(|e| {
+            warn!("Failed to convert WebP to PNG: {:?}", e);
+            AdvancedCommonWebError::from_error(e)
+          })?;
 
       let converted_metadata = resolve_file_metadata(&converted, Some("image/png"))
-          .ok_or_else(|| anyhow!("Failed to determine file type after WebP→PNG conversion"))?;
+          .ok_or_else(|| {
+            warn!("Failed to determine file type after WebP→PNG conversion");
+            AdvancedCommonWebError::server_error_with_message(
+              "Failed to determine file type after WebP→PNG conversion")
+          })?;
 
       info!("Converted file type: {}, extension: {:?}",
         converted_metadata.mime_type, converted_metadata.file_extension);
@@ -93,16 +114,28 @@ async fn upload_single_image_bytes(
   file_bytes: &[u8],
   mime_type: &str,
   file_extension: FileExtension,
-) -> AnyhowResult<MediaFileToken> {
+) -> Result<MediaFileToken, AdvancedCommonWebError> {
 
   let media_file_type = MediaFileType::try_from_mime_type(mime_type)
-      .ok_or_else(|| anyhow!("Unsupported media file type: {}", mime_type))?;
+      .ok_or_else(|| {
+        warn!("Unsupported media file type: {}", mime_type);
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Unsupported media file type: {}", mime_type))
+      })?;
 
   let extension_with_period = file_extension.extension_with_period();
 
   let file_size_bytes = file_bytes.len();
-  let file_hash = sha256_hash_bytes(&file_bytes)?;
-  let image_info = ImageInfo::decode_image_from_bytes(&file_bytes)?;
+  let file_hash = sha256_hash_bytes(&file_bytes)
+      .map_err(|e| {
+        warn!("Failed to hash image bytes: {:?}", e);
+        AdvancedCommonWebError::from_anyhow_error(e)
+      })?;
+  let image_info = ImageInfo::decode_image_from_bytes(&file_bytes)
+      .map_err(|e| {
+        warn!("Failed to decode image info: {:?}", e);
+        AdvancedCommonWebError::from_error(e)
+      })?;
 
   let public_upload_path = MediaFileBucketPath::generate_new(PREFIX, Some(&extension_with_period));
 
@@ -112,7 +145,11 @@ async fn upload_single_image_bytes(
     public_upload_path.get_full_object_path_str(),
     file_bytes.as_ref(),
     mime_type)
-      .await?;
+      .await
+      .map_err(|e| {
+        warn!("Failed to upload image to bucket: {:?}", e);
+        AdvancedCommonWebError::from_anyhow_error(e)
+      })?;
 
   let media_token = MediaFileInsertBuilder::new()
       .maybe_creator_user(job.maybe_creator_user_token.as_ref())
@@ -130,8 +167,12 @@ async fn upload_single_image_bytes(
       .frame_height(image_info.height())
       .checksum_sha2(&file_hash)
       .insert_pool(&server_state.mysql_pool)
-      .await?;
-  
+      .await
+      .map_err(|err| {
+        warn!("Failed to insert image media file record: {:?}", err);
+        AdvancedCommonWebError::from_error(err)
+      })?;
+
   info!("Image media file uploaded with token: {}", media_token);
 
   Ok(media_token)
diff --git a/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_images_payload.rs b/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_images_payload.rs
index 029a348c41..f0c689faac 100644
--- a/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_images_payload.rs
+++ b/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_images_payload.rs
@@ -1,12 +1,11 @@
+use crate::http_server::common_responses::advanced_common_web_error::AdvancedCommonWebError;
 use crate::http_server::endpoints::webhooks::process_success::resolve_file_metadata::resolve_file_metadata;
 use crate::state::server_state::ServerState;
 use crate::util::http_download_url_to_bytes::http_download_url_to_bytes;
-use anyhow::anyhow;
 use bucket_paths::legacy::typified_paths::public::media_files::bucket_file_path::MediaFileBucketPath;
 use enums::by_table::media_files::media_file_class::MediaFileClass;
 use enums::by_table::media_files::media_file_origin_category::MediaFileOriginCategory;
 use enums::by_table::media_files::media_file_type::MediaFileType;
-use errors::AnyhowResult;
 use fal_client::webhook_api::hydrated::hydrated_webhook_contents::ImagesData;
 use hashing::sha256::sha256_hash_bytes::sha256_hash_bytes;
 use images::encoding::webp_bytes_to_png_bytes::webp_bytes_to_png_bytes;
@@ -24,7 +23,7 @@ pub async fn process_images_payload(
   images_data: &[ImagesData],
   job: &FalJobDetails,
   server_state: &ServerState,
-) -> AnyhowResult<(Option<MediaFileToken>, Option<BatchGenerationToken>)> {
+) -> Result<(Option<MediaFileToken>, Option<BatchGenerationToken>), AdvancedCommonWebError> {
 
   let mut maybe_media_token = None;
 
@@ -52,15 +51,22 @@ async fn upload_image(
   server_state: &ServerState,
   image: &ImagesData,
   maybe_batch_token: Option<&BatchGenerationToken>,
-) -> AnyhowResult<MediaFileToken> {
+) -> Result<MediaFileToken, AdvancedCommonWebError> {
   let image_url = image.url
       .as_deref()
-      .ok_or_else(|| anyhow!("no `url` in image payload"))?;
+      .ok_or_else(|| {
+        warn!("No `url` in image payload");
+        AdvancedCommonWebError::server_error_with_message("no `url` in image payload")
+      })?;
 
   // Download with a retry if the first attempt returns suspiciously few bytes.
   let mut file_bytes = http_download_url_to_bytes(image_url)
       .await
-      .map_err(|e| anyhow!("Failed to download image: {:?}", e))?;
+      .map_err(|e| {
+        warn!("Failed to download image from {}: {:?}", image_url, e);
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Failed to download image: {:?}", e))
+      })?;
 
   if file_bytes.len() <= 10 {
     warn!(
@@ -70,16 +76,25 @@ async fn upload_image(
     );
     file_bytes = http_download_url_to_bytes(image_url)
         .await
-        .map_err(|e| anyhow!("Failed to download image on retry: {:?}", e))?;
+        .map_err(|e| {
+          warn!("Failed to download image on retry from {}: {:?}", image_url, e);
+          AdvancedCommonWebError::server_error_with_message(
+            &format!("Failed to download image on retry: {:?}", e))
+        })?;
   }
 
   // Resolve mime type: magic bytes first, fal content_type as fallback.
   let metadata = resolve_file_metadata(&file_bytes, image.content_type.as_deref())
-      .ok_or_else(|| anyhow!(
-        "Could not determine file type for image (bytes: {}, fal content_type: {:?})",
-        file_bytes.len(),
-        image.content_type,
-      ))?;
+      .ok_or_else(|| {
+        warn!(
+          "Could not determine file type for image (bytes: {}, fal content_type: {:?})",
+          file_bytes.len(),
+          image.content_type,
+        );
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Could not determine file type for image (bytes: {}, fal content_type: {:?})",
+            file_bytes.len(), image.content_type))
+      })?;
 
   info!("File type: {}, extension: {:?}, source: {:?}",
     metadata.mime_type, metadata.file_extension, metadata.source);
@@ -88,10 +103,18 @@ async fn upload_image(
     FileExtension::Webp => {
       info!("Artcraft can't handle WebP images yet; converting to PNG...");
 
-      let converted = webp_bytes_to_png_bytes(&file_bytes)?;
+      let converted = webp_bytes_to_png_bytes(&file_bytes)
+          .map_err(|e| {
+            warn!("Failed to convert WebP to PNG: {:?}", e);
+            AdvancedCommonWebError::from_error(e)
+          })?;
 
       let converted_metadata = resolve_file_metadata(&converted, Some("image/png"))
-          .ok_or_else(|| anyhow!("Failed to determine file type after WebP→PNG conversion"))?;
+          .ok_or_else(|| {
+            warn!("Failed to determine file type after WebP→PNG conversion");
+            AdvancedCommonWebError::server_error_with_message(
+              "Failed to determine file type after WebP→PNG conversion")
+          })?;
 
       info!("Converted file type: {}, extension: {:?}",
         converted_metadata.mime_type, converted_metadata.file_extension);
@@ -99,7 +122,6 @@ async fn upload_image(
       upload_image_bytes(
         job,
         server_state,
-        image,
         &converted,
         &converted_metadata.mime_type,
         converted_metadata.file_extension,
@@ -110,7 +132,6 @@ async fn upload_image(
       upload_image_bytes(
         job,
         server_state,
-        image,
         &file_bytes,
         &metadata.mime_type,
         metadata.file_extension,
@@ -123,23 +144,34 @@ async fn upload_image(
 async fn upload_image_bytes(
   job: &FalJobDetails,
   server_state: &ServerState,
-  _image: &ImagesData,
   file_bytes: &[u8],
   mime_type: &str,
   file_extension: FileExtension,
   maybe_batch_token: Option<&BatchGenerationToken>,
-) -> AnyhowResult<MediaFileToken> {
+) -> Result<MediaFileToken, AdvancedCommonWebError> {
 
   let media_file_type = MediaFileType::try_from_mime_type(mime_type)
-      .ok_or_else(|| anyhow!("Unsupported media file type: {}", mime_type))?;
+      .ok_or_else(|| {
+        warn!("Unsupported media file type: {}", mime_type);
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Unsupported media file type: {}", mime_type))
+      })?;
 
   info!("MediaFileType: {:?}", media_file_type);
 
   let extension_with_period = file_extension.extension_with_period();
 
   let file_size_bytes = file_bytes.len();
-  let file_hash = sha256_hash_bytes(&file_bytes)?;
-  let image_info = ImageInfo::decode_image_from_bytes(&file_bytes)?;
+  let file_hash = sha256_hash_bytes(&file_bytes)
+      .map_err(|e| {
+        warn!("Failed to hash image bytes: {:?}", e);
+        AdvancedCommonWebError::from_anyhow_error(e)
+      })?;
+  let image_info = ImageInfo::decode_image_from_bytes(&file_bytes)
+      .map_err(|e| {
+        warn!("Failed to decode image info: {:?}", e);
+        AdvancedCommonWebError::from_error(e)
+      })?;
 
   let public_upload_path = MediaFileBucketPath::generate_new(PREFIX, Some(&extension_with_period));
 
@@ -149,7 +181,11 @@ async fn upload_image_bytes(
     public_upload_path.get_full_object_path_str(),
     file_bytes.as_ref(),
     mime_type)
-      .await?;
+      .await
+      .map_err(|e| {
+        warn!("Failed to upload image to bucket: {:?}", e);
+        AdvancedCommonWebError::from_anyhow_error(e)
+      })?;
 
   let mut query_builder = MediaFileInsertBuilder::new()
       .maybe_creator_user(job.maybe_creator_user_token.as_ref())
@@ -173,7 +209,11 @@ async fn upload_image_bytes(
 
   let media_token = query_builder
       .insert_pool(&server_state.mysql_pool)
-      .await?;
+      .await
+      .map_err(|e| {
+        warn!("Failed to insert image media file record: {:?}", e);
+        AdvancedCommonWebError::from_error(e)
+      })?;
 
   info!("Image media file uploaded with token: {} ; possible batch token: {:?}",
     media_token, maybe_batch_token);
diff --git a/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_model_glb_payload.rs b/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_model_glb_payload.rs
index ee6184551d..2d668c8846 100644
--- a/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_model_glb_payload.rs
+++ b/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_model_glb_payload.rs
@@ -1,13 +1,12 @@
+use crate::http_server::common_responses::advanced_common_web_error::AdvancedCommonWebError;
 use crate::http_server::endpoints::webhooks::process_success::resolve_file_metadata::resolve_file_metadata;
 use crate::state::server_state::ServerState;
 use crate::util::http_download_url_to_bytes::http_download_url_to_bytes;
-use anyhow::anyhow;
 use bucket_paths::legacy::typified_paths::public::media_files::bucket_file_path::MediaFileBucketPath;
 use enums::by_table::media_files::media_file_class::MediaFileClass;
 use enums::by_table::media_files::media_file_engine_category::MediaFileEngineCategory;
 use enums::by_table::media_files::media_file_origin_category::MediaFileOriginCategory;
 use enums::by_table::media_files::media_file_type::MediaFileType;
-use errors::AnyhowResult;
 use fal_client::webhook_api::hydrated::hydrated_webhook_contents::{ModelGlbData, ThumbnailData};
 use hashing::sha256::sha256_hash_bytes::sha256_hash_bytes;
 use log::{info, warn};
@@ -20,7 +19,7 @@ const PREFIX : Option<&str> = Some("artcraft_");
 
 /*
   Example payload, from Hunyuan 3d 3.0,
-  
+
   {
     "model_glb": {
       "url": "https://v3b.fal.media/files/b/0a8afeff/8uc6VVLTpmVrupLqxxwOg_model.glb",
@@ -52,7 +51,7 @@ const PREFIX : Option<&str> = Some("artcraft_");
     },
     "seed": null
   }
-  
+
 */
 
 pub async fn process_model_glb_payload(
@@ -60,15 +59,21 @@ pub async fn process_model_glb_payload(
   maybe_thumbnail_data: Option<&ThumbnailData>,
   job: &FalJobDetails,
   server_state: &ServerState,
-) -> AnyhowResult<MediaFileToken> {
+) -> Result<MediaFileToken, AdvancedCommonWebError> {
   let mesh_url = model_glb_data.url
       .as_deref()
-      .ok_or_else(|| anyhow!("no `url` in model glb payload"))?;
+      .ok_or_else(|| {
+        warn!("No `url` in model glb payload");
+        AdvancedCommonWebError::server_error_with_message("no `url` in model glb payload")
+      })?;
 
   // Download with a retry if the first attempt returns suspiciously few bytes.
   let mut file_bytes = http_download_url_to_bytes(mesh_url)
       .await
-      .map_err(|e| anyhow!("Failed to download mesh: {:?}", e))?;
+      .map_err(|err| {
+        warn!("Failed to download mesh from {}: {:?}", mesh_url, err);
+        AdvancedCommonWebError::from_anyhow_error(err)
+      })?;
 
   if file_bytes.len() <= 10 {
     warn!(
@@ -78,28 +83,45 @@ pub async fn process_model_glb_payload(
     );
     file_bytes = http_download_url_to_bytes(mesh_url)
         .await
-        .map_err(|e| anyhow!("Failed to download mesh on retry: {:?}", e))?;
+        .map_err(|e| {
+          warn!("Failed to download mesh on retry from {}: {:?}", mesh_url, e);
+          AdvancedCommonWebError::server_error_with_message(
+            &format!("Failed to download mesh on retry: {:?}", e))
+        })?;
   }
 
   // Resolve mime type: magic bytes first, fal content_type as fallback.
   let metadata = resolve_file_metadata(&file_bytes, model_glb_data.content_type.as_deref())
-      .ok_or_else(|| anyhow!(
-        "Could not determine file type for mesh (bytes: {}, fal content_type: {:?})",
-        file_bytes.len(),
-        model_glb_data.content_type,
-      ))?;
+      .ok_or_else(|| {
+        warn!(
+          "Could not determine file type for mesh (bytes: {}, fal content_type: {:?})",
+          file_bytes.len(),
+          model_glb_data.content_type,
+        );
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Could not determine file type for mesh (bytes: {}, fal content_type: {:?})",
+            file_bytes.len(), model_glb_data.content_type))
+      })?;
 
   let mime_type = metadata.mime_type.as_str();
 
   info!("Mime type of mesh: {}, source: {:?}", mime_type, metadata.source);
 
   let media_file_type = MediaFileType::try_from_mime_type(mime_type)
-      .ok_or_else(|| anyhow!("Unsupported media file type: {}", mime_type))?;
+      .ok_or_else(|| {
+        warn!("Unsupported media file type: {}", mime_type);
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Unsupported media file type: {}", mime_type))
+      })?;
 
   let extension_with_period = metadata.file_extension.extension_with_period();
 
   let file_size_bytes = file_bytes.len();
-  let file_hash = sha256_hash_bytes(&file_bytes)?;
+  let file_hash = sha256_hash_bytes(&file_bytes)
+      .map_err(|e| {
+        warn!("Failed to hash mesh bytes: {:?}", e);
+        AdvancedCommonWebError::from_anyhow_error(e)
+      })?;
 
   let public_upload_path = MediaFileBucketPath::generate_new(PREFIX, Some(&extension_with_period));
 
@@ -109,7 +131,11 @@ pub async fn process_model_glb_payload(
     public_upload_path.get_full_object_path_str(),
     file_bytes.as_ref(),
     &mime_type)
-      .await?;
+      .await
+      .map_err(|e| {
+        warn!("Failed to upload mesh to bucket: {:?}", e);
+        AdvancedCommonWebError::from_anyhow_error(e)
+      })?;
 
   let media_token = MediaFileInsertBuilder::new()
       .maybe_creator_user(job.maybe_creator_user_token.as_ref())
@@ -126,17 +152,21 @@ pub async fn process_model_glb_payload(
       .maybe_prompt_token(job.maybe_prompt_token.as_ref())
       .checksum_sha2(&file_hash)
       .insert_pool(&server_state.mysql_pool)
-      .await?;
-  
+      .await
+      .map_err(|e| {
+        warn!("Failed to insert glb media file record: {:?}", e);
+        AdvancedCommonWebError::from_error(e)
+      })?;
+
   info!("Glb media file uploaded with token: {}", media_token);
-  
+
   let result = try_to_attach_thumbnail(
     maybe_thumbnail_data,
     job,
     server_state,
     &media_token,
   ).await;
-  
+
   // NB: Fail open
   if let Err(err) = result {
     warn!("Could not attach thumbnail as cover image to media file: {:?}", err);
@@ -150,20 +180,31 @@ async fn try_to_attach_thumbnail(
   job: &FalJobDetails,
   server_state: &ServerState,
   glb_media_token: &MediaFileToken,
-) -> AnyhowResult<()> {
+) -> Result<(), AdvancedCommonWebError> {
   let thumbnail_data = maybe_thumbnail_data
-      .ok_or_else(|| anyhow!("no thumbnail data in extracted contents"))?;
+      .ok_or_else(|| {
+        warn!("No thumbnail data in extracted contents");
+        AdvancedCommonWebError::server_error_with_message(
+          "no thumbnail data in extracted contents")
+      })?;
 
   info!("Fal Thumbnail Data: {:?}", thumbnail_data);
 
   let thumbnail_url = thumbnail_data.url
       .as_deref()
-      .ok_or_else(|| anyhow!("no `url` in thumbnail payload"))?;
+      .ok_or_else(|| {
+        warn!("No `url` in thumbnail payload");
+        AdvancedCommonWebError::server_error_with_message("no `url` in thumbnail payload")
+      })?;
 
   // Download with a retry if the first attempt returns suspiciously few bytes.
   let mut file_bytes = http_download_url_to_bytes(thumbnail_url)
       .await
-      .map_err(|e| anyhow!("Failed to download thumbnail image: {:?}", e))?;
+      .map_err(|e| {
+        warn!("Failed to download thumbnail image from {}: {:?}", thumbnail_url, e);
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Failed to download thumbnail image: {:?}", e))
+      })?;
 
   if file_bytes.len() <= 10 {
     warn!(
@@ -173,28 +214,45 @@ async fn try_to_attach_thumbnail(
     );
     file_bytes = http_download_url_to_bytes(thumbnail_url)
         .await
-        .map_err(|e| anyhow!("Failed to download thumbnail on retry: {:?}", e))?;
+        .map_err(|e| {
+          warn!("Failed to download thumbnail on retry from {}: {:?}", thumbnail_url, e);
+          AdvancedCommonWebError::server_error_with_message(
+            &format!("Failed to download thumbnail on retry: {:?}", e))
+        })?;
   }
 
   // Resolve mime type: magic bytes first, fal content_type as fallback.
   let metadata = resolve_file_metadata(&file_bytes, thumbnail_data.content_type.as_deref())
-      .ok_or_else(|| anyhow!(
-        "Could not determine file type for thumbnail (bytes: {}, fal content_type: {:?})",
-        file_bytes.len(),
-        thumbnail_data.content_type,
-      ))?;
+      .ok_or_else(|| {
+        warn!(
+          "Could not determine file type for thumbnail (bytes: {}, fal content_type: {:?})",
+          file_bytes.len(),
+          thumbnail_data.content_type,
+        );
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Could not determine file type for thumbnail (bytes: {}, fal content_type: {:?})",
+            file_bytes.len(), thumbnail_data.content_type))
+      })?;
 
   let mime_type = metadata.mime_type.as_str();
 
   info!("Mime type of thumbnail image: {}, source: {:?}", mime_type, metadata.source);
 
   let media_file_type = MediaFileType::try_from_mime_type(mime_type)
-      .ok_or_else(|| anyhow!("Unsupported media file type: {}", mime_type))?;
+      .ok_or_else(|| {
+        warn!("Unsupported thumbnail media file type: {}", mime_type);
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Unsupported media file type: {}", mime_type))
+      })?;
 
   let extension_with_period = metadata.file_extension.extension_with_period();
 
   let file_size_bytes = file_bytes.len();
-  let file_hash = sha256_hash_bytes(&file_bytes)?;
+  let file_hash = sha256_hash_bytes(&file_bytes)
+      .map_err(|e| {
+        warn!("Failed to hash thumbnail bytes: {:?}", e);
+        AdvancedCommonWebError::from_anyhow_error(e)
+      })?;
 
   let public_upload_path = MediaFileBucketPath::generate_new(PREFIX, Some(&extension_with_period));
 
@@ -204,7 +262,11 @@ async fn try_to_attach_thumbnail(
     public_upload_path.get_full_object_path_str(),
     file_bytes.as_ref(),
     &mime_type)
-      .await?;
+      .await
+      .map_err(|e| {
+        warn!("Failed to upload thumbnail to bucket: {:?}", e);
+        AdvancedCommonWebError::from_anyhow_error(e)
+      })?;
 
   let thumbnail_media_token = MediaFileInsertBuilder::new()
       .maybe_creator_user(job.maybe_creator_user_token.as_ref())
@@ -222,7 +284,11 @@ async fn try_to_attach_thumbnail(
       .is_intermediate_system_file(true)
       .checksum_sha2(&file_hash)
       .insert_pool(&server_state.mysql_pool)
-      .await?;
+      .await
+      .map_err(|e| {
+        warn!("Failed to insert thumbnail media file record: {:?}", e);
+        AdvancedCommonWebError::from_error(e)
+      })?;
 
   let query_result = set_media_file_cover_image(UpdateArgs {
     media_file_token: glb_media_token,
@@ -230,5 +296,9 @@ async fn try_to_attach_thumbnail(
     mysql_pool: &server_state.mysql_pool,
   }).await;
 
+  if let Err(err) = query_result {
+    warn!("Failed to set cover image on media file {}: {:?}", glb_media_token, err);
+  }
+
   Ok(())
 }
diff --git a/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_model_mesh_payload.rs b/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_model_mesh_payload.rs
index 21426c8c84..482c8f3ad3 100644
--- a/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_model_mesh_payload.rs
+++ b/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_model_mesh_payload.rs
@@ -1,13 +1,12 @@
+use crate::http_server::common_responses::advanced_common_web_error::AdvancedCommonWebError;
 use crate::http_server::endpoints::webhooks::process_success::resolve_file_metadata::resolve_file_metadata;
 use crate::state::server_state::ServerState;
 use crate::util::http_download_url_to_bytes::http_download_url_to_bytes;
-use anyhow::anyhow;
 use bucket_paths::legacy::typified_paths::public::media_files::bucket_file_path::MediaFileBucketPath;
 use enums::by_table::media_files::media_file_class::MediaFileClass;
 use enums::by_table::media_files::media_file_engine_category::MediaFileEngineCategory;
 use enums::by_table::media_files::media_file_origin_category::MediaFileOriginCategory;
 use enums::by_table::media_files::media_file_type::MediaFileType;
-use errors::AnyhowResult;
 use fal_client::webhook_api::hydrated::hydrated_webhook_contents::ModelMeshData;
 use hashing::sha256::sha256_hash_bytes::sha256_hash_bytes;
 use log::{info, warn};
@@ -21,15 +20,21 @@ pub async fn process_model_mesh_payload(
   model_mesh_data: &ModelMeshData,
   job: &FalJobDetails,
   server_state: &ServerState,
-) -> AnyhowResult<MediaFileToken> {
+) -> Result<MediaFileToken, AdvancedCommonWebError> {
   let mesh_url = model_mesh_data.url
       .as_deref()
-      .ok_or_else(|| anyhow!("no `url` in model mesh payload"))?;
+      .ok_or_else(|| {
+        warn!("No `url` in model mesh payload");
+        AdvancedCommonWebError::server_error_with_message("no `url` in model mesh payload")
+      })?;
 
   // Download with a retry if the first attempt returns suspiciously few bytes.
   let mut file_bytes = http_download_url_to_bytes(mesh_url)
       .await
-      .map_err(|e| anyhow!("Failed to download mesh: {:?}", e))?;
+      .map_err(|err| {
+        warn!("Failed to download mesh from {}: {:?}", mesh_url, err);
+        AdvancedCommonWebError::from_anyhow_error(err)
+      })?;
 
   if file_bytes.len() <= 10 {
     warn!(
@@ -39,28 +44,44 @@ pub async fn process_model_mesh_payload(
     );
     file_bytes = http_download_url_to_bytes(mesh_url)
         .await
-        .map_err(|e| anyhow!("Failed to download mesh on retry: {:?}", e))?;
+        .map_err(|err| {
+          warn!("Failed to download mesh on retry from {}: {:?}", mesh_url, err);
+          AdvancedCommonWebError::from_anyhow_error(err)
+        })?;
   }
 
   // Resolve mime type: magic bytes first, fal content_type as fallback.
   let metadata = resolve_file_metadata(&file_bytes, model_mesh_data.content_type.as_deref())
-      .ok_or_else(|| anyhow!(
-        "Could not determine file type for mesh (bytes: {}, fal content_type: {:?})",
-        file_bytes.len(),
-        model_mesh_data.content_type,
-      ))?;
+      .ok_or_else(|| {
+        warn!(
+          "Could not determine file type for mesh (bytes: {}, fal content_type: {:?})",
+          file_bytes.len(),
+          model_mesh_data.content_type,
+        );
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Could not determine file type for mesh (bytes: {}, fal content_type: {:?})",
+            file_bytes.len(), model_mesh_data.content_type))
+      })?;
 
   let mime_type = metadata.mime_type.as_str();
 
   info!("Mime type of mesh: {}, source: {:?}", mime_type, metadata.source);
 
   let media_file_type = MediaFileType::try_from_mime_type(mime_type)
-      .ok_or_else(|| anyhow!("Unsupported media file type: {}", mime_type))?;
+      .ok_or_else(|| {
+        warn!("Unsupported media file type: {}", mime_type);
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Unsupported media file type: {}", mime_type))
+      })?;
 
   let extension_with_period = metadata.file_extension.extension_with_period();
 
   let file_size_bytes = file_bytes.len();
-  let file_hash = sha256_hash_bytes(&file_bytes)?;
+  let file_hash = sha256_hash_bytes(&file_bytes)
+      .map_err(|err| {
+        warn!("Failed to hash mesh bytes: {:?}", err);
+        AdvancedCommonWebError::from_anyhow_error(err)
+      })?;
 
   let public_upload_path = MediaFileBucketPath::generate_new(PREFIX, Some(&extension_with_period));
 
@@ -70,7 +91,11 @@ pub async fn process_model_mesh_payload(
     public_upload_path.get_full_object_path_str(),
     file_bytes.as_ref(),
     &mime_type)
-      .await?;
+      .await
+      .map_err(|err| {
+        warn!("Failed to upload mesh to bucket: {:?}", err);
+        AdvancedCommonWebError::from_anyhow_error(err)
+      })?;
 
   let media_token = MediaFileInsertBuilder::new()
       .maybe_creator_user(job.maybe_creator_user_token.as_ref())
@@ -87,8 +112,12 @@ pub async fn process_model_mesh_payload(
       .maybe_prompt_token(job.maybe_prompt_token.as_ref())
       .checksum_sha2(&file_hash)
       .insert_pool(&server_state.mysql_pool)
-      .await?;
-  
+      .await
+      .map_err(|err| {
+        warn!("Failed to insert mesh media file record: {:?}", err);
+        AdvancedCommonWebError::from_error(err)
+      })?;
+
   info!("Mesh media file uploaded with token: {}", media_token);
 
   Ok(media_token)
diff --git a/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_video_payload.rs b/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_video_payload.rs
index fb0d07129e..f5dc1249f8 100644
--- a/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_video_payload.rs
+++ b/crates/service/web/storyteller_web/src/http_server/endpoints/webhooks/process_success/process_video_payload.rs
@@ -1,12 +1,11 @@
+use crate::http_server::common_responses::advanced_common_web_error::AdvancedCommonWebError;
 use crate::http_server::endpoints::webhooks::process_success::resolve_file_metadata::resolve_file_metadata;
 use crate::state::server_state::ServerState;
 use crate::util::http_download_url_to_bytes::http_download_url_to_bytes;
-use anyhow::anyhow;
 use bucket_paths::legacy::typified_paths::public::media_files::bucket_file_path::MediaFileBucketPath;
 use enums::by_table::media_files::media_file_class::MediaFileClass;
 use enums::by_table::media_files::media_file_origin_category::MediaFileOriginCategory;
 use enums::by_table::media_files::media_file_type::MediaFileType;
-use errors::AnyhowResult;
 use fal_client::webhook_api::hydrated::hydrated_webhook_contents::VideoData;
 use filesys::path_to_string::path_to_string;
 use hashing::sha256::sha256_hash_bytes::sha256_hash_bytes;
@@ -25,15 +24,21 @@ pub async fn process_video_payload(
   video_data: &VideoData,
   job: &FalJobDetails,
   server_state: &ServerState,
-) -> AnyhowResult<MediaFileToken> {
+) -> Result<MediaFileToken, AdvancedCommonWebError> {
   let video_url = video_data.url
       .as_deref()
-      .ok_or_else(|| anyhow!("no `url` in video payload"))?;
+      .ok_or_else(|| {
+        warn!("No `url` in video payload");
+        AdvancedCommonWebError::server_error_with_message("no `url` in video payload")
+      })?;
 
   // Download with a retry if the first attempt returns suspiciously few bytes.
   let mut file_bytes = http_download_url_to_bytes(video_url)
       .await
-      .map_err(|e| anyhow!("Failed to download video: {:?}", e))?;
+      .map_err(|err| {
+        warn!("Failed to download video from {}: {:?}", video_url, err);
+        AdvancedCommonWebError::from_anyhow_error(err)
+      })?;
 
   if file_bytes.len() <= 10 {
     warn!(
@@ -43,16 +48,24 @@ pub async fn process_video_payload(
     );
     file_bytes = http_download_url_to_bytes(video_url)
         .await
-        .map_err(|e| anyhow!("Failed to download video on retry: {:?}", e))?;
+        .map_err(|err| {
+          warn!("Failed to download video on retry from {}: {:?}", video_url, err);
+          AdvancedCommonWebError::from_anyhow_error(err)
+        })?;
   }
 
   // Resolve mime type: magic bytes first, fal content_type as fallback.
   let metadata = resolve_file_metadata(&file_bytes, video_data.content_type.as_deref())
-      .ok_or_else(|| anyhow!(
-        "Could not determine file type for video (bytes: {}, fal content_type: {:?})",
-        file_bytes.len(),
-        video_data.content_type,
-      ))?;
+      .ok_or_else(|| {
+        warn!(
+          "Could not determine file type for video (bytes: {}, fal content_type: {:?})",
+          file_bytes.len(),
+          video_data.content_type,
+        );
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Could not determine file type for video (bytes: {}, fal content_type: {:?})",
+            file_bytes.len(), video_data.content_type))
+      })?;
 
   info!("File type: {}, extension: {:?}, source: {:?}",
     metadata.mime_type, metadata.file_extension, metadata.source);
@@ -60,26 +73,34 @@ pub async fn process_video_payload(
   let mime_type = metadata.mime_type.as_str();
 
   let media_file_type = MediaFileType::try_from_mime_type(mime_type)
-      .ok_or_else(|| anyhow!("Unsupported media file type: {}", mime_type))?;
+      .ok_or_else(|| {
+        warn!("Unsupported media file type: {}", mime_type);
+        AdvancedCommonWebError::server_error_with_message(
+          &format!("Unsupported media file type: {}", mime_type))
+      })?;
 
   let extension_with_period = metadata.file_extension.extension_with_period();
 
   let file_size_bytes = file_bytes.len();
-  let file_hash = sha256_hash_bytes(&file_bytes)?;
+  let file_hash = sha256_hash_bytes(&file_bytes)
+      .map_err(|e| {
+        warn!("Failed to hash video bytes: {:?}", e);
+        AdvancedCommonWebError::from_anyhow_error(e)
+      })?;
 
   let mut maybe_duration_millis = None;
   let mut maybe_frame_width = None;
   let mut maybe_frame_height = None;
-  
+
   if let Ok(mut file) = NamedTempFile::new() {
-    // NB: Fallible 
+    // NB: Fallible
     let _r = file.write_all(&file_bytes);
-    
+
     if let Ok(video_info) = ffprobe_get_info(&file.path()) {
       maybe_duration_millis = video_info.duration
           .as_ref()
           .map(|duration| duration.millis as u64);
-      
+
       maybe_frame_width = video_info.dimensions
           .as_ref()
           .map(|ref dims| dims.width as u32);
@@ -98,7 +119,11 @@ pub async fn process_video_payload(
     public_upload_path.get_full_object_path_str(),
     file_bytes.as_ref(),
     &mime_type)
-      .await?;
+      .await
+      .map_err(|e| {
+        warn!("Failed to upload video to bucket: {:?}", e);
+        AdvancedCommonWebError::from_anyhow_error(e)
+      })?;
 
   let media_token = MediaFileInsertBuilder::new()
       .maybe_creator_user(job.maybe_creator_user_token.as_ref())
@@ -117,8 +142,12 @@ pub async fn process_video_payload(
       .checksum_sha2(&file_hash)
       .maybe_prompt_token(job.maybe_prompt_token.as_ref())
       .insert_pool(&server_state.mysql_pool)
-      .await?;
-  
+      .await
+      .map_err(|e| {
+        warn!("Failed to insert video media file record: {:?}", e);
+        AdvancedCommonWebError::from_error(e)
+      })?;
+
   info!("Video media file uploaded with token: {}", media_token);
 
   let thumbnail_task_result =