diff --git a/actions/deleteLeaflet.ts b/actions/deleteLeaflet.ts
index d6108def..a25acb45 100644
--- a/actions/deleteLeaflet.ts
+++ b/actions/deleteLeaflet.ts
@@ -23,11 +23,13 @@ export async function deleteLeaflet(permission_token: PermissionToken) {
   // Check publication and document ownership in one query
   let { data: tokenData } = await supabaseServerClient
     .from("permission_tokens")
-    .select(`
+    .select(
+      `
       id,
       leaflets_in_publications(publication, publications!inner(identity_did)),
       leaflets_to_documents(document, documents!inner(uri))
-    `)
+    `,
+    )
     .eq("id", permission_token.id)
     .single();
 
@@ -36,28 +38,34 @@ export async function deleteLeaflet(permission_token: PermissionToken) {
     const leafletInPubs = tokenData.leaflets_in_publications || [];
     if (leafletInPubs.length > 0) {
       if (!identity) {
-        throw new Error("Unauthorized: You must be logged in to delete a leaflet in a publication");
+        throw new Error(
+          "Unauthorized: You must be logged in to delete a leaflet in a publication",
+        );
       }
       const isOwner = leafletInPubs.some(
-        (pub: any) => pub.publications.identity_did === identity.atp_did
+        (pub: any) => pub.publications.identity_did === identity.atp_did,
       );
       if (!isOwner) {
-        throw new Error("Unauthorized: You must own the publication to delete this leaflet");
+        throw new Error(
+          "Unauthorized: You must own the publication to delete this leaflet",
+        );
       }
     }
 
     // Check if there's a standalone published document
-    const leafletDocs = tokenData.leaflets_to_documents || [];
-    if (leafletDocs.length > 0) {
-      if (!identity) {
-        throw new Error("Unauthorized: You must be logged in to delete a published leaflet");
+    const leafletDoc = tokenData.leaflets_to_documents;
+    if (leafletDoc && leafletDoc.document) {
+      if (!identity || !identity.atp_did) {
+        throw new Error(
+          "Unauthorized: You must be logged in to delete a published leaflet",
+        );
       }
-      for (let leafletDoc of leafletDocs) {
-        const docUri = leafletDoc.documents?.uri;
-        // Extract the DID from the document URI (format: at://did:plc:xxx/...)
-        if (docUri && !docUri.includes(identity.atp_did)) {
-          throw new Error("Unauthorized: You must own the published document to delete this leaflet");
-        }
+      const docUri = leafletDoc.documents?.uri;
+      // Extract the DID from the document URI (format: at://did:plc:xxx/...)
+      if (docUri && !docUri.includes(identity.atp_did)) {
+        throw new Error(
+          "Unauthorized: You must own the published document to delete this leaflet",
+        );
       }
     }
   }
@@ -73,9 +81,9 @@ export async function deleteLeaflet(permission_token: PermissionToken) {
       .where(eq(permission_tokens.id, permission_token.id));
 
     if (!token?.permission_token_rights?.write) return;
-    await tx
-      .delete(entities)
-      .where(eq(entities.set, token.permission_token_rights.entity_set));
+    const entitySet = token.permission_token_rights.entity_set;
+    if (!entitySet) return;
+    await tx.delete(entities).where(eq(entities.set, entitySet));
     await tx
       .delete(permission_tokens)
       .where(eq(permission_tokens.id, permission_token.id));
diff --git a/actions/publications/moveLeafletToPublication.ts b/actions/publications/moveLeafletToPublication.ts
index a3ee8c62..160ddc4a 100644
--- a/actions/publications/moveLeafletToPublication.ts
+++ b/actions/publications/moveLeafletToPublication.ts
@@ -11,6 +11,8 @@ export async function moveLeafletToPublication(
 ) {
   let identity = await getIdentityData();
   if (!identity || !identity.atp_did) return null;
+
+  // Verify publication ownership
   let { data: publication } = await supabaseServerClient
     .from("publications")
     .select("*")
@@ -18,6 +20,7 @@ export async function moveLeafletToPublication(
     .single();
   if (publication?.identity_did !== identity.atp_did) return;
 
+  // Save as a publication draft
   await supabaseServerClient.from("leaflets_in_publications").insert({
     publication: publication_uri,
     leaflet: leaflet_id,
diff --git a/actions/publications/saveLeafletDraft.ts b/actions/publications/saveLeafletDraft.ts
new file mode 100644
index 00000000..c6650672
--- /dev/null
+++ b/actions/publications/saveLeafletDraft.ts
@@ -0,0 +1,26 @@
+"use server";
+
+import { getIdentityData } from "actions/getIdentityData";
+import { supabaseServerClient } from "supabase/serverClient";
+
+export async function saveLeafletDraft(
+  leaflet_id: string,
+  metadata: { title: string; description: string },
+  entitiesToDelete: string[],
+) {
+  let identity = await getIdentityData();
+  if (!identity || !identity.atp_did) return null;
+
+  // Save as a looseleaf draft in leaflets_to_documents with null document
+  await supabaseServerClient.from("leaflets_to_documents").upsert({
+    leaflet: leaflet_id,
+    document: null,
+    title: metadata.title,
+    description: metadata.description,
+  });
+
+  await supabaseServerClient
+    .from("entities")
+    .delete()
+    .in("id", entitiesToDelete);
+}
diff --git a/app/(home-pages)/home/HomeLayout.tsx b/app/(home-pages)/home/HomeLayout.tsx
index 568a6e7e..744b4d5d 100644
--- a/app/(home-pages)/home/HomeLayout.tsx
+++ b/app/(home-pages)/home/HomeLayout.tsx
@@ -136,7 +136,7 @@ export function HomeLeafletList(props: {
             (acc, tok) => {
               let title =
                 tok.permission_tokens.leaflets_in_publications[0]?.title ||
-                tok.permission_tokens.leaflets_to_documents[0]?.title;
+                tok.permission_tokens.leaflets_to_documents?.title;
               if (title) acc[tok.permission_tokens.root_entity] = title;
               return acc;
             },
@@ -233,7 +233,7 @@ export function LeafletList(props: {
             value={{
               ...leaflet,
               leaflets_in_publications: leaflet.leaflets_in_publications || [],
-              leaflets_to_documents: leaflet.leaflets_to_documents || [],
+              leaflets_to_documents: leaflet.leaflets_to_documents || null,
               blocked_by_admin: null,
               custom_domain_routes: [],
             }}
@@ -292,7 +292,7 @@ function useSearchedLeaflets(
     ({ token: leaflet, archived: archived }) => {
       let published =
         !!leaflet.leaflets_in_publications?.find((l) => l.doc) ||
-        !!leaflet.leaflets_to_documents?.find((l) => l.document);
+        !!leaflet.leaflets_to_documents?.document;
       let drafts = !!leaflet.leaflets_in_publications?.length && !published;
       let docs = !leaflet.leaflets_in_publications?.length && !archived;
       // If no filters are active, show all
diff --git a/app/(home-pages)/home/page.tsx b/app/(home-pages)/home/page.tsx
index 5408ab37..9b783167 100644
--- a/app/(home-pages)/home/page.tsx
+++ b/app/(home-pages)/home/page.tsx
@@ -30,7 +30,7 @@ export default async function Home() {
           (acc, tok) => {
             let title =
               tok.permission_tokens.leaflets_in_publications[0]?.title ||
-              tok.permission_tokens.leaflets_to_documents[0]?.title;
+              tok.permission_tokens.leaflets_to_documents?.title;
             if (title) acc[tok.permission_tokens.root_entity] = title;
             return acc;
           },
diff --git a/app/(home-pages)/looseleafs/LooseleafsLayout.tsx b/app/(home-pages)/looseleafs/LooseleafsLayout.tsx
index fd1ba95b..c96140ac 100644
--- a/app/(home-pages)/looseleafs/LooseleafsLayout.tsx
+++ b/app/(home-pages)/looseleafs/LooseleafsLayout.tsx
@@ -111,7 +111,7 @@ export const LooseleafList = (props: {
             (acc, tok) => {
               let title =
                 tok.permission_tokens.leaflets_in_publications[0]?.title ||
-                tok.permission_tokens.leaflets_to_documents[0]?.title;
+                tok.permission_tokens.leaflets_to_documents?.title;
               if (title) acc[tok.permission_tokens.root_entity] = title;
               return acc;
             },
@@ -127,7 +127,9 @@ export const LooseleafList = (props: {
   let leaflets: Leaflet[] = identity
     ? identity.permission_token_on_homepage
         .filter(
-          (ptoh) => ptoh.permission_tokens.leaflets_to_documents.length > 0,
+          (ptoh) =>
+            ptoh.permission_tokens.leaflets_to_documents &&
+            ptoh.permission_tokens.leaflets_to_documents.document,
         )
         .map((ptoh) => ({
           added_at: ptoh.created_at,
diff --git a/app/(home-pages)/looseleafs/page.tsx b/app/(home-pages)/looseleafs/page.tsx
index 9ae9f7b3..1b2fc02c 100644
--- a/app/(home-pages)/looseleafs/page.tsx
+++ b/app/(home-pages)/looseleafs/page.tsx
@@ -34,7 +34,7 @@ export default async function Home() {
           (acc, tok) => {
             let title =
               tok.permission_tokens.leaflets_in_publications[0]?.title ||
-              tok.permission_tokens.leaflets_to_documents[0]?.title;
+              tok.permission_tokens.leaflets_to_documents?.title;
             if (title) acc[tok.permission_tokens.root_entity] = title;
             return acc;
           },
diff --git a/app/[leaflet_id]/actions/HomeButton.tsx b/app/[leaflet_id]/actions/HomeButton.tsx
index 54d54753..14cae86f 100644
--- a/app/[leaflet_id]/actions/HomeButton.tsx
+++ b/app/[leaflet_id]/actions/HomeButton.tsx
@@ -53,7 +53,7 @@ const AddToHomeButton = (props: {}) => {
               archived: null,
               permission_tokens: {
                 ...permission_token,
-                leaflets_to_documents: [],
+                leaflets_to_documents: null,
                 leaflets_in_publications: [],
               },
             });
diff --git a/app/[leaflet_id]/actions/PublishButton.tsx b/app/[leaflet_id]/actions/PublishButton.tsx
index 4098d1ff..2cde46a8 100644
--- a/app/[leaflet_id]/actions/PublishButton.tsx
+++ b/app/[leaflet_id]/actions/PublishButton.tsx
@@ -37,6 +37,7 @@ import * as base64 from "base64-js";
 import { YJSFragmentToString } from "components/Blocks/TextBlock/RenderYJSFragment";
 import { BlueskyLogin } from "app/login/LoginForm";
 import { moveLeafletToPublication } from "actions/publications/moveLeafletToPublication";
+import { saveLeafletDraft } from "actions/publications/saveLeafletDraft";
 import { AddTiny } from "components/Icons/AddTiny";
 
 export const PublishButton = (props: { entityID: string }) => {
@@ -176,7 +177,7 @@ const PublishToPublicationButton = (props: { entityID: string }) => {
           <hr className="border-border-light mt-3 mb-2" />
 
           <div className="flex gap-2 items-center place-self-end">
-            {selectedPub !== "looseleaf" && selectedPub && (
+            {selectedPub && selectedPub !== "create" && (
               <SaveAsDraftButton
                 selectedPub={selectedPub}
                 leafletId={permission_token.id}
@@ -229,12 +230,23 @@ const SaveAsDraftButton = (props: {
         if (props.selectedPub === "create") return;
         e.preventDefault();
         setIsLoading(true);
-        await moveLeafletToPublication(
-          props.leafletId,
-          props.selectedPub,
-          props.metadata,
-          props.entitiesToDelete,
-        );
+
+        // Use different actions for looseleaf vs publication
+        if (props.selectedPub === "looseleaf") {
+          await saveLeafletDraft(
+            props.leafletId,
+            props.metadata,
+            props.entitiesToDelete,
+          );
+        } else {
+          await moveLeafletToPublication(
+            props.leafletId,
+            props.selectedPub,
+            props.metadata,
+            props.entitiesToDelete,
+          );
+        }
+
         await Promise.all([rep?.pull(), mutate()]);
         setIsLoading(false);
       }}
diff --git a/app/[leaflet_id]/publish/page.tsx b/app/[leaflet_id]/publish/page.tsx
index 9ee5917c..2b760235 100644
--- a/app/[leaflet_id]/publish/page.tsx
+++ b/app/[leaflet_id]/publish/page.tsx
@@ -76,11 +76,11 @@ export default async function PublishLeafletPage(props: Props) {
   // Get title and description from either source
   let title =
     data.leaflets_in_publications[0]?.title ||
-    data.leaflets_to_documents[0]?.title ||
+    data.leaflets_to_documents?.title ||
     decodeURIComponent((await props.searchParams).title || "");
   let description =
     data.leaflets_in_publications[0]?.description ||
-    data.leaflets_to_documents[0]?.description ||
+    data.leaflets_to_documents?.description ||
     decodeURIComponent((await props.searchParams).description || "");
 
   let agent = new AtpAgent({ service: "https://public.api.bsky.app" });
diff --git a/app/lish/[did]/[publication]/dashboard/PublishedPostsLists.tsx b/app/lish/[did]/[publication]/dashboard/PublishedPostsLists.tsx
index d7388a53..fa9af3cd 100644
--- a/app/lish/[did]/[publication]/dashboard/PublishedPostsLists.tsx
+++ b/app/lish/[did]/[publication]/dashboard/PublishedPostsLists.tsx
@@ -107,7 +107,7 @@ export function PublishedPostsList(props: {
                                     : null,
                                 },
                               ],
-                              leaflets_to_documents: [],
+                              leaflets_to_documents: null,
                               blocked_by_admin: null,
                               custom_domain_routes: [],
                             }}
diff --git a/components/ActionBar/Publications.tsx b/components/ActionBar/Publications.tsx
index e6465cb2..f2165154 100644
--- a/components/ActionBar/Publications.tsx
+++ b/components/ActionBar/Publications.tsx
@@ -24,7 +24,9 @@ export const PublicationButtons = (props: {
 }) => {
   let { identity } = useIdentityData();
   let hasLooseleafs = identity?.permission_token_on_homepage.find(
-    (f) => f.permission_tokens.leaflets_to_documents[0],
+    (f) =>
+      f.permission_tokens.leaflets_to_documents &&
+      f.permission_tokens.leaflets_to_documents.document,
   );
   console.log(hasLooseleafs);
 
diff --git a/components/PageSWRDataProvider.tsx b/components/PageSWRDataProvider.tsx
index ab866443..3d5a4e46 100644
--- a/components/PageSWRDataProvider.tsx
+++ b/components/PageSWRDataProvider.tsx
@@ -90,16 +90,20 @@ export function useLeafletPublicationStatus() {
   const publishedInPublication = data.leaflets_in_publications?.find(
     (l) => l.doc,
   );
-  const publishedStandalone = data.leaflets_to_documents?.find(
-    (l) => !!l.documents,
-  );
+  const publishedStandalone =
+    data.leaflets_to_documents && data.leaflets_to_documents.documents
+      ? data.leaflets_to_documents
+      : null;
 
   const documentUri =
     publishedInPublication?.documents?.uri ?? publishedStandalone?.document;
 
   // Compute the full post URL for sharing
   let postShareLink: string | undefined;
-  if (publishedInPublication?.publications && publishedInPublication.documents) {
+  if (
+    publishedInPublication?.publications &&
+    publishedInPublication.documents
+  ) {
     // Published in a publication - use publication URL + document rkey
     const docUri = new AtUri(publishedInPublication.documents.uri);
     postShareLink = `${getPublicationURL(publishedInPublication.publications)}/${docUri.rkey}`;
diff --git a/src/utils/getPublicationMetadataFromLeafletData.ts b/src/utils/getPublicationMetadataFromLeafletData.ts
index 32483bd4..2de33b7a 100644
--- a/src/utils/getPublicationMetadataFromLeafletData.ts
+++ b/src/utils/getPublicationMetadataFromLeafletData.ts
@@ -32,19 +32,43 @@ export function getPublicationMetadataFromLeafletData(
       (p) => p.leaflets_in_publications?.length,
     )?.leaflets_in_publications?.[0];
 
-  // If not found, check for standalone documents
-  let standaloneDoc =
-    data?.leaflets_to_documents?.[0] ||
-    data?.permission_token_rights[0].entity_sets?.permission_tokens.find(
-      (p) => p.leaflets_to_documents?.length,
-    )?.leaflets_to_documents?.[0];
-  if (!pubData && standaloneDoc) {
+  // If not found, check for standalone documents (looseleafs)
+  let standaloneDoc = data?.leaflets_to_documents;
+
+  // Only use standaloneDoc if it exists and has meaningful data
+  // (either published with a document, or saved as draft with a title)
+  if (
+    !pubData &&
+    standaloneDoc &&
+    (standaloneDoc.document || standaloneDoc.title)
+  ) {
     // Transform standalone document data to match the expected format
     pubData = {
       ...standaloneDoc,
       publications: null, // No publication for standalone docs
       doc: standaloneDoc.document,
+      leaflet: data.id,
     };
   }
+
+  // Also check nested permission tokens for looseleafs
+  if (!pubData) {
+    let nestedStandaloneDoc =
+      data?.permission_token_rights[0].entity_sets?.permission_tokens?.find(
+        (p) =>
+          p.leaflets_to_documents &&
+          (p.leaflets_to_documents.document || p.leaflets_to_documents.title),
+      )?.leaflets_to_documents;
+
+    if (nestedStandaloneDoc) {
+      pubData = {
+        ...nestedStandaloneDoc,
+        publications: null,
+        doc: nestedStandaloneDoc.document,
+        leaflet: data.id,
+      };
+    }
+  }
+
   return pubData;
 }
diff --git a/supabase/database.types.ts b/supabase/database.types.ts
index 43d56b03..ad8d757e 100644
--- a/supabase/database.types.ts
+++ b/supabase/database.types.ts
@@ -631,21 +631,21 @@ export type Database = {
         Row: {
           created_at: string
           description: string
-          document: string
+          document: string | null
           leaflet: string
           title: string
         }
         Insert: {
           created_at?: string
           description?: string
-          document: string
+          document?: string | null
           leaflet: string
           title?: string
         }
         Update: {
           created_at?: string
           description?: string
-          document?: string
+          document?: string | null
           leaflet?: string
           title?: string
         }
@@ -660,7 +660,7 @@ export type Database = {
           {
             foreignKeyName: "leaflets_to_documents_leaflet_fkey"
             columns: ["leaflet"]
-            isOneToOne: false
+            isOneToOne: true
             referencedRelation: "permission_tokens"
             referencedColumns: ["id"]
           },