diff --git a/__tests__/cmds/docs/prune.test.ts b/__tests__/cmds/docs/prune.test.ts
index 8b71ca2db..05c840b41 100644
--- a/__tests__/cmds/docs/prune.test.ts
+++ b/__tests__/cmds/docs/prune.test.ts
@@ -88,7 +88,7 @@ describe('rdme docs:prune', () => {
         confirm: true,
         version,
       })
-    ).resolves.toBe('🗑️ successfully deleted `this-doc-should-be-missing-in-folder`.');
+    ).resolves.toBe('🗑️  successfully deleted `this-doc-should-be-missing-in-folder`.');
 
     apiMocks.done();
     versionMock.done();
@@ -116,7 +116,7 @@ describe('rdme docs:prune', () => {
         key,
         version,
       })
-    ).resolves.toBe('🗑️ successfully deleted `this-doc-should-be-missing-in-folder`.');
+    ).resolves.toBe('🗑️  successfully deleted `this-doc-should-be-missing-in-folder`.');
 
     apiMocks.done();
     versionMock.done();
@@ -151,7 +151,7 @@ describe('rdme docs:prune', () => {
         version,
       })
     ).resolves.toBe(
-      '🗑️ successfully deleted `this-doc-should-be-missing-in-folder`.\n🗑️ successfully deleted `this-child-is-also-missing`.'
+      '🗑️  successfully deleted `this-child-is-also-missing`.\n🗑️  successfully deleted `this-doc-should-be-missing-in-folder`.'
     );
 
     apiMocks.done();
diff --git a/src/lib/deleteDoc.ts b/src/lib/deleteDoc.ts
index 974a89f1e..9d3d4ce81 100644
--- a/src/lib/deleteDoc.ts
+++ b/src/lib/deleteDoc.ts
@@ -36,5 +36,5 @@ export default async function deleteDoc(
     ),
   })
     .then(handleRes)
-    .then(() => `🗑️ successfully deleted \`${slug}\`.`);
+    .then(() => `🗑️  successfully deleted \`${slug}\`.`);
 }
diff --git a/src/lib/getDocs.ts b/src/lib/getDocs.ts
index 91d5cfd46..fa76403ce 100644
--- a/src/lib/getDocs.ts
+++ b/src/lib/getDocs.ts
@@ -24,6 +24,11 @@ function flatten(data: Document[][]): Document[] {
       });
     }
   });
+
+  // Docs with children cannot be deleted unless the children are deleted first,
+  // so move those parent docs to the back of the list
+  allDocs.sort(a => (a.children?.length ? 1 : -1));
+
   return allDocs;
 }