diff --git a/packages/router-core/src/new-process-route-tree.ts b/packages/router-core/src/new-process-route-tree.ts
index 6978b071ce..2841c17c73 100644
--- a/packages/router-core/src/new-process-route-tree.ts
+++ b/packages/router-core/src/new-process-route-tree.ts
@@ -190,6 +190,7 @@ export function parseSegment(
  * @param route The current route to parse.
  * @param start The starting index for parsing within the route's full path.
  * @param node The current segment node in the trie to populate.
+ * @param sortable Dynamic sibling arrays that need sorting. Each array is recorded once when it reaches length 2.
  * @param onRoute Callback invoked for each route processed.
  */
 function parseSegments<TRouteLike extends RouteLike>(
@@ -199,6 +200,7 @@ function parseSegments<TRouteLike extends RouteLike>(
   start: number,
   node: AnySegmentNode<TRouteLike>,
   depth: number,
+  sortable?: Array<Array<DynamicSegmentNode<TRouteLike>>>,
   onRoute?: (route: TRouteLike) => void,
 ) {
   onRoute?.(route)
@@ -291,6 +293,9 @@ function parseSegments<TRouteLike extends RouteLike>(
             next.parent = node
             node.dynamic ??= []
             node.dynamic.push(next)
+            if (node.dynamic.length === 2) {
+              sortable?.push(node.dynamic)
+            }
           }
           break
         }
@@ -333,6 +338,9 @@ function parseSegments<TRouteLike extends RouteLike>(
             next.depth = depth
             node.optional ??= []
             node.optional.push(next)
+            if (node.optional.length === 2) {
+              sortable?.push(node.optional)
+            }
           }
           break
         }
@@ -363,6 +371,9 @@ function parseSegments<TRouteLike extends RouteLike>(
           next.depth = depth
           node.wildcard ??= []
           node.wildcard.push(next)
+          if (node.wildcard.length === 2) {
+            sortable?.push(node.wildcard)
+          }
         }
       }
       node = nextNode
@@ -420,6 +431,7 @@ function parseSegments<TRouteLike extends RouteLike>(
         cursor,
         node,
         depth,
+        sortable,
         onRoute,
       )
     }
@@ -464,42 +476,6 @@ function sortDynamic(
   return 0
 }
 
-function sortTreeNodes(node: SegmentNode<RouteLike>) {
-  if (node.pathless) {
-    for (const child of node.pathless) {
-      sortTreeNodes(child)
-    }
-  }
-  if (node.static) {
-    for (const child of node.static.values()) {
-      sortTreeNodes(child)
-    }
-  }
-  if (node.staticInsensitive) {
-    for (const child of node.staticInsensitive.values()) {
-      sortTreeNodes(child)
-    }
-  }
-  if (node.dynamic?.length) {
-    node.dynamic.sort(sortDynamic)
-    for (const child of node.dynamic) {
-      sortTreeNodes(child)
-    }
-  }
-  if (node.optional?.length) {
-    node.optional.sort(sortDynamic)
-    for (const child of node.optional) {
-      sortTreeNodes(child)
-    }
-  }
-  if (node.wildcard?.length) {
-    node.wildcard.sort(sortDynamic)
-    for (const child of node.wildcard) {
-      sortTreeNodes(child)
-    }
-  }
-}
-
 function createStaticNode<T extends RouteLike>(
   fullPath: string,
 ): StaticSegmentNode<T> {
@@ -663,10 +639,13 @@ export function processRouteMasks<
 ) {
   const segmentTree = createStaticNode<TRouteLike>('/')
   const data = new Uint16Array(6)
+  const sortable: Array<Array<DynamicSegmentNode<TRouteLike>>> = []
   for (const route of routeList) {
-    parseSegments(false, data, route, 1, segmentTree, 0)
+    parseSegments(false, data, route, 1, segmentTree, 0, sortable)
+  }
+  for (const nodes of sortable) {
+    nodes.sort(sortDynamic)
   }
-  sortTreeNodes(segmentTree)
   processedTree.masksTree = segmentTree
   processedTree.flatCache = createLRUCache<
     string,
@@ -791,32 +770,44 @@ export function processRouteTree<
   const data = new Uint16Array(6)
   const routesById = {} as Record<string, TRouteLike>
   const routesByPath = {} as Record<string, TRouteLike>
+  const sortable: Array<Array<DynamicSegmentNode<TRouteLike>>> = []
   let index = 0
-  parseSegments(caseSensitive, data, routeTree, 1, segmentTree, 0, (route) => {
-    initRoute?.(route, index)
+  parseSegments(
+    caseSensitive,
+    data,
+    routeTree,
+    1,
+    segmentTree,
+    0,
+    sortable,
+    (route) => {
+      initRoute?.(route, index)
+
+      if (route.id in routesById) {
+        if (process.env.NODE_ENV !== 'production') {
+          throw new Error(
+            `Invariant failed: Duplicate routes found with id: ${String(route.id)}`,
+          )
+        }
 
-    if (route.id in routesById) {
-      if (process.env.NODE_ENV !== 'production') {
-        throw new Error(
-          `Invariant failed: Duplicate routes found with id: ${String(route.id)}`,
-        )
+        invariant()
       }
 
-      invariant()
-    }
-
-    routesById[route.id] = route
+      routesById[route.id] = route
 
-    if (index !== 0 && route.path) {
-      const trimmedFullPath = trimPathRight(route.fullPath)
-      if (!routesByPath[trimmedFullPath] || route.fullPath.endsWith('/')) {
-        routesByPath[trimmedFullPath] = route
+      if (index !== 0 && route.path) {
+        const trimmedFullPath = trimPathRight(route.fullPath)
+        if (!routesByPath[trimmedFullPath] || route.fullPath.endsWith('/')) {
+          routesByPath[trimmedFullPath] = route
+        }
       }
-    }
 
-    index++
-  })
-  sortTreeNodes(segmentTree)
+      index++
+    },
+  )
+  for (const nodes of sortable) {
+    nodes.sort(sortDynamic)
+  }
   const processedTree: ProcessedTree<TRouteLike, any, any> = {
     segmentTree,
     singleCache: createLRUCache<string, AnySegmentNode<any>>(1000),
diff --git a/packages/router-core/tests/new-process-route-tree.test.ts b/packages/router-core/tests/new-process-route-tree.test.ts
index d93581355e..1703c69042 100644
--- a/packages/router-core/tests/new-process-route-tree.test.ts
+++ b/packages/router-core/tests/new-process-route-tree.test.ts
@@ -114,6 +114,10 @@ describe('findRouteMatch', () => {
         const tree = makeTree(['/a/{-$b}b', '/a/{-$b}'])
         expect(findRouteMatch('/a/bbb', tree)?.route.id).toBe('/a/{-$b}b')
       })
+      it('prefix+suffix optional wins when declared after plain optional', () => {
+        const tree = makeTree(['/a/{-$b}', '/a/b{-$b}b'])
+        expect(findRouteMatch('/a/bbb', tree)?.route.id).toBe('/a/b{-$b}b')
+      })
 
       it('prefix+suffix wildcard wins over plain wildcard', () => {
         const tree = makeTree(['/a/b{$}b', '/a/$'])
@@ -127,6 +131,10 @@ describe('findRouteMatch', () => {
         const tree = makeTree(['/a/{$}b', '/a/$'])
         expect(findRouteMatch('/a/bbb', tree)?.route.id).toBe('/a/{$}b')
       })
+      it('sorts a third, more specific wildcard declared last', () => {
+        const tree = makeTree(['/a/$', '/a/b{$}', '/a/b{$}b'])
+        expect(findRouteMatch('/a/bbb', tree)?.route.id).toBe('/a/b{$}b')
+      })
     })
 
     describe('prefix / suffix lengths', () => {
@@ -1672,4 +1680,29 @@ describe('processRouteMasks', { sequential: true }, () => {
     expect(res?.route.from).toBe('/a/b/{$}.txt')
     expect(res?.rawParams).toEqual({ '*': 'file/path', _splat: 'file/path' })
   })
+  it('sorts competing route masks declared least-specific first', () => {
+    const localTree = processRouteTree(routeTree).processedTree
+    processRouteMasks(
+      [
+        { from: '/dynamic/$param', routeTree },
+        { from: '/dynamic/prefix{$param}', routeTree },
+        { from: '/optional/{-$param}', routeTree },
+        { from: '/optional/prefix{-$param}', routeTree },
+        { from: '/wildcard/$', routeTree },
+        { from: '/wildcard/prefix{$}', routeTree },
+        { from: '/wildcard/prefix{$}.txt', routeTree },
+      ],
+      localTree,
+    )
+
+    expect(findFlatMatch('/dynamic/prefixvalue', localTree)?.route.from).toBe(
+      '/dynamic/prefix{$param}',
+    )
+    expect(findFlatMatch('/optional/prefixvalue', localTree)?.route.from).toBe(
+      '/optional/prefix{-$param}',
+    )
+    expect(
+      findFlatMatch('/wildcard/prefixvalue.txt', localTree)?.route.from,
+    ).toBe('/wildcard/prefix{$}.txt')
+  })
 })