diff --git a/README.md b/README.md
index 0a09980..4cd4aeb 100644
--- a/README.md
+++ b/README.md
@@ -510,6 +510,15 @@ A secure API key can be generated by any password generator.
         $ cp -r exports/2023-07-08T22:26:21.194126713Z sled-repo
         ```
     4. Starting pict-rs
+- `POST /internal/prepare_upgrade?force={force}` Spawn a background task that will attempt to prepare the database
+    for the 0.5 upgrade. This process will attempt to generate metadata for all original uploads if
+    needed.
+
+    This endpoint can be hit repeatedly to check the progress of the preparations.
+
+    Optionally, the `force` query parameter can be passed with a value of `true` in order to make
+    pict-rs spawn another task if the current one seems stuck.
+
 
 Additionally, all endpoints support setting deadlines, after which the request will cease
 processing. To enable deadlines for your requests, you can set the `X-Request-Deadline` header to an
diff --git a/src/lib.rs b/src/lib.rs
index f2e9ab9..410df01 100644
--- a/src/lib.rs
+++ b/src/lib.rs
@@ -114,14 +114,22 @@ async fn ensure_details<R: FullRepo, S: Store + 'static>(
         return Err(UploadError::MissingAlias.into());
     };
 
-    let details = repo.details(&identifier).await?;
+    ensure_details_identifier(repo, store, &identifier, details_hint(alias)).await
+}
+
+async fn ensure_details_identifier<R: FullRepo, S: Store + 'static>(
+    repo: &R,
+    store: &S,
+    identifier: &S::Identifier,
+    hint: Option<ValidInputType>,
+) -> Result<Details, Error> {
+    let details = repo.details(identifier).await?;
 
     if let Some(details) = details {
         tracing::debug!("details exist");
         Ok(details)
     } else {
         tracing::debug!("generating new details from {:?}", identifier);
-        let hint = details_hint(alias);
         let new_details = Details::from_store(
             store.clone(),
             identifier.clone(),
@@ -130,7 +138,7 @@ async fn ensure_details<R: FullRepo, S: Store + 'static>(
         )
         .await?;
         tracing::debug!("storing details for {:?}", identifier);
-        repo.relate_details(&identifier, &new_details).await?;
+        repo.relate_details(identifier, &new_details).await?;
         tracing::debug!("stored");
         Ok(new_details)
     }
@@ -693,25 +701,9 @@ async fn process<R: FullRepo, S: Store + 'static>(
         .await?;
 
     if let Some(identifier) = identifier_opt {
-        let details = repo.details(&identifier).await?;
+        let hint = Some(ValidInputType::from_format(format));
 
-        let details = if let Some(details) = details {
-            tracing::debug!("details exist");
-            details
-        } else {
-            tracing::debug!("generating new details from {:?}", identifier);
-            let new_details = Details::from_store(
-                (**store).clone(),
-                identifier.clone(),
-                Some(ValidInputType::from_format(format)),
-                CONFIG.media.process_timeout,
-            )
-            .await?;
-            tracing::debug!("storing details for {:?}", identifier);
-            repo.relate_details(&identifier, &new_details).await?;
-            tracing::debug!("stored");
-            new_details
-        };
+        let details = ensure_details_identifier(&repo, &store, &identifier, hint).await?;
 
         return ranged_file_resp(&store, identifier, range, details, not_found).await;
     }
@@ -790,25 +782,9 @@ async fn process_head<R: FullRepo, S: Store + 'static>(
         .await?;
 
     if let Some(identifier) = identifier_opt {
-        let details = repo.details(&identifier).await?;
+        let hint = Some(ValidInputType::from_format(format));
 
-        let details = if let Some(details) = details {
-            tracing::debug!("details exist");
-            details
-        } else {
-            tracing::debug!("generating new details from {:?}", identifier);
-            let new_details = Details::from_store(
-                (**store).clone(),
-                identifier.clone(),
-                Some(ValidInputType::from_format(format)),
-                CONFIG.media.process_timeout,
-            )
-            .await?;
-            tracing::debug!("storing details for {:?}", identifier);
-            repo.relate_details(&identifier, &new_details).await?;
-            tracing::debug!("stored");
-            new_details
-        };
+        let details = ensure_details_identifier(&repo, &store, &identifier, hint).await?;
 
         return ranged_file_head_resp(&store, identifier, range, details).await;
     }
@@ -1043,6 +1019,50 @@ fn srv_head(
     builder
 }
 
+#[derive(serde::Serialize)]
+struct UpgradeResponse {
+    complete: bool,
+    progress: u64,
+    total: u64,
+}
+
+#[derive(Debug, serde::Deserialize)]
+struct UpgradeQuery {
+    force: bool,
+}
+
+#[tracing::instrument(name = "Prepare for 0.5 upgrade", skip(repo))]
+async fn prepare_upgrade<R: FullRepo>(
+    repo: web::Data<R>,
+    query: Option<web::Query<UpgradeQuery>>,
+) -> Result<HttpResponse, Error> {
+    let total = repo.size().await?;
+
+    let progress = if let Some(progress) = repo.get("upgrade-preparations-progress").await? {
+        progress
+            .as_ref()
+            .try_into()
+            .map(u64::from_be_bytes)
+            .unwrap_or(0)
+    } else {
+        0
+    };
+
+    let complete = repo.get("upgrade-preparations-complete").await?.is_some();
+
+    let started = repo.get("upgrade-preparations-started").await?.is_some();
+
+    if !started || query.is_some_and(|q| q.force) {
+        queue::queue_prepare_upgrade(&repo).await?;
+    }
+
+    Ok(HttpResponse::Ok().json(UpgradeResponse {
+        complete,
+        progress,
+        total,
+    }))
+}
+
 #[tracing::instrument(name = "Spawning variant cleanup", skip(repo))]
 async fn clean_variants<R: FullRepo>(repo: web::Data<R>) -> Result<HttpResponse, Error> {
     queue::cleanup_all_variants(&repo).await?;
@@ -1242,6 +1262,9 @@ fn configure_endpoints<
                 .service(web::resource("/aliases").route(web::get().to(aliases::<R>)))
                 .service(web::resource("/identifier").route(web::get().to(identifier::<R, S>)))
                 .service(web::resource("/set_not_found").route(web::post().to(set_not_found::<R>)))
+                .service(
+                    web::resource("/prepare_upgrade").route(web::post().to(prepare_upgrade::<R>)),
+                )
                 .configure(extra_config),
         );
 }
diff --git a/src/queue.rs b/src/queue.rs
index aa4fdcf..5f32ce6 100644
--- a/src/queue.rs
+++ b/src/queue.rs
@@ -76,6 +76,7 @@ enum Process {
         process_path: PathBuf,
         process_args: Vec<String>,
     },
+    PrepareUpgrade,
 }
 
 pub(crate) async fn cleanup_alias<R: QueueRepo>(
@@ -124,6 +125,12 @@ pub(crate) async fn cleanup_all_variants<R: QueueRepo>(repo: &R) -> Result<(), E
     Ok(())
 }
 
+pub(crate) async fn queue_prepare_upgrade<R: QueueRepo>(repo: &R) -> Result<(), Error> {
+    let job = serde_json::to_vec(&Process::PrepareUpgrade)?;
+    repo.push(PROCESS_QUEUE, job.into()).await?;
+    Ok(())
+}
+
 pub(crate) async fn queue_ingest<R: QueueRepo>(
     repo: &R,
     identifier: Vec<u8>,
diff --git a/src/queue/process.rs b/src/queue/process.rs
index 66ec37b..a0f9083 100644
--- a/src/queue/process.rs
+++ b/src/queue/process.rs
@@ -7,7 +7,7 @@ use crate::{
     serde_str::Serde,
     store::{Identifier, Store},
 };
-use futures_util::TryStreamExt;
+use futures_util::{StreamExt, TryStreamExt};
 use reqwest_middleware::ClientWithMiddleware;
 use std::path::PathBuf;
 use url::Url;
@@ -62,6 +62,7 @@ where
                     )
                     .await?
                 }
+                Process::PrepareUpgrade => prepare_upgrade(repo, store).await?,
             },
             Err(e) => {
                 tracing::warn!("Invalid job: {}", format!("{e}"));
@@ -225,3 +226,60 @@ async fn generate<R: FullRepo, S: Store + 'static>(
 
     Ok(())
 }
+
+#[tracing::instrument(skip_all)]
+async fn prepare_upgrade<R: FullRepo + 'static, S: Store + 'static>(
+    repo: &R,
+    store: &S,
+) -> Result<(), Error> {
+    repo.set("upgrade-preparations-started", b"1".to_vec().into())
+        .await?;
+
+    let mut hashes = std::pin::pin!(repo.hashes().await);
+
+    let mut count: u64 = 0;
+
+    while let Some(res) = hashes.next().await {
+        match res {
+            Ok(hash) => {
+                let repo = repo.clone();
+                let store = store.clone();
+
+                let res = actix_rt::spawn(async move {
+                    if let Some(identifier) = repo.identifier(hash).await? {
+                        crate::ensure_details_identifier(&repo, &store, &identifier, None).await?;
+                    }
+
+                    repo.set(
+                        "upgrade-preparations-progress",
+                        Vec::from(count.to_be_bytes()).into(),
+                    )
+                    .await?;
+
+                    Ok(()) as Result<(), Error>
+                })
+                .await;
+
+                match res {
+                    Ok(Ok(_)) => {}
+                    Ok(Err(e)) => {
+                        tracing::warn!("Failed to ensure details for a hash: {e}");
+                    }
+                    Err(_) => {
+                        tracing::warn!("Panic while ensuring details for a hash");
+                    }
+                }
+            }
+            Err(e) => {
+                tracing::warn!("Skipping upgrade check for a hash: {e}");
+            }
+        }
+
+        count += 1;
+    }
+
+    repo.set("upgrade-preparations-complete", b"1".to_vec().into())
+        .await?;
+
+    Ok(())
+}