diff --git a/Sources/ContainerBuild/BuildFSSync.swift b/Sources/ContainerBuild/BuildFSSync.swift
index c5a5288f2..e97724e5d 100644
--- a/Sources/ContainerBuild/BuildFSSync.swift
+++ b/Sources/ContainerBuild/BuildFSSync.swift
@@ -272,11 +272,12 @@ actor BuildFSSync: BuildPipelineHandler {
             destination: tarURL,
             writerConfiguration: writerCfg
         ) { url in
-            guard let rel = try? url.relativeChildPath(to: contextDir) else {
+            let resolvedURL = url.resolvingSymlinksInPath()
+            guard let rel = try? resolvedURL.relativeChildPath(to: self.contextDir) else {
                 return nil
             }
 
-            guard let parent = try? url.deletingLastPathComponent().relativeChildPath(to: self.contextDir) else {
+            guard let parent = try? resolvedURL.deletingLastPathComponent().relativeChildPath(to: self.contextDir) else {
                 return nil
             }
 
diff --git a/Tests/ContainerBuildTests/BuildFSSyncTests.swift b/Tests/ContainerBuildTests/BuildFSSyncTests.swift
index 5d6d607d2..4fbecc5f9 100644
--- a/Tests/ContainerBuildTests/BuildFSSyncTests.swift
+++ b/Tests/ContainerBuildTests/BuildFSSyncTests.swift
@@ -394,4 +394,58 @@ import Testing
         let secretLeak = infos.first { $0.name.hasSuffix("secret.txt") }
         #expect(secretLeak == nil, "no entry for the external file should appear in walk() results: \(infos.map { $0.name })")
     }
+
+    // MARK: - walk(): tar mode symlinked contextDir prefix regression test (#2037)
+
+    @Test func testWalkTarIncludesFilesWhenContextDirUsesSymlinkedPrefix() async throws {
+        // Create context directory using a symlinked path prefix (e.g. /tmp on macOS -> /private/tmp)
+        let symlinkBase = URL(fileURLWithPath: "/tmp/" + UUID().uuidString)
+        try fm.createDirectory(at: symlinkBase, withIntermediateDirectories: true)
+        defer { try? fm.removeItem(at: symlinkBase) }
+
+        let sampleFile = symlinkBase.appendingPathComponent("staged-run.sh")
+        try write("#!/bin/sh\n", to: sampleFile)
+
+        let fssync = try BuildFSSync(symlinkBase)
+
+        var continuation: AsyncStream<ClientStream>.Continuation!
+        let stream = AsyncStream<ClientStream> { continuation = $0 }
+
+        var packet = BuildTransfer()
+        packet.id = UUID().uuidString
+        packet.source = "."
+        packet.metadata = [
+            "followpaths": "staged-run.sh",
+            "mode": "tar",
+        ]
+
+        try await fssync.walk(continuation, packet, "build-repro")
+        continuation.finish()
+
+        var receivedData = Data()
+        for await resp in stream {
+            if !resp.buildTransfer.data.isEmpty {
+                receivedData.append(resp.buildTransfer.data)
+            }
+        }
+
+        #expect(!receivedData.isEmpty, "tar archive data should not be empty for context under symlinked prefix")
+
+        // Unpack tar to temporary directory and verify staged-run.sh is explicitly present inside the archive
+        let unpackDir = URL.temporaryDirectory.appendingPathComponent(UUID().uuidString)
+        let archiveFile = URL.temporaryDirectory.appendingPathComponent(UUID().uuidString + ".tar")
+        try receivedData.write(to: archiveFile)
+        defer {
+            try? fm.removeItem(at: unpackDir)
+            try? fm.removeItem(at: archiveFile)
+        }
+
+        let archiveReader = try ArchiveReader(url: archiveFile)
+        var entryPaths = [String]()
+        for entry in try archiveReader.readEntries() {
+            entryPaths.append(entry.path)
+        }
+
+        #expect(entryPaths.contains("staged-run.sh"), "staged-run.sh must be explicitly present in tar archive entries: \(entryPaths)")
+    }
 }
diff --git a/Tests/IntegrationTests/Build/TestCLIBuilder.swift b/Tests/IntegrationTests/Build/TestCLIBuilder.swift
index 95d4f74f8..7c5a65860 100644
--- a/Tests/IntegrationTests/Build/TestCLIBuilder.swift
+++ b/Tests/IntegrationTests/Build/TestCLIBuilder.swift
@@ -1030,4 +1030,33 @@ struct TestCLIBuilder {
             try f.assertImageBuilt(image)
         }
     }
+
+    /// Regression test for issue #2037: `container build` with single file COPY and no `.dockerignore`.
+    /// Verifies context files under symlinked parent paths (like /tmp on macOS) are transferred properly.
+    @Test func testBuildContextSingleFileCOPY() async throws {
+        try await ContainerFixture.with { f in
+            let dir = try f.createTempDir()
+            let dockerfile = """
+                FROM ghcr.io/linuxcontainers/alpine:3.20
+                COPY staged-run.sh /run.sh
+                RUN cat /run.sh
+                """
+            try f.createContext(
+                dir: dir,
+                dockerfile: dockerfile,
+                context: [
+                    .file("staged-run.sh", content: .data(Data("#!/bin/sh\necho hello\n".utf8)))
+                ])
+
+            let image = "registry.local/build-context-single-file:\(UUID().uuidString)"
+            try f.build(tag: image, contextDir: dir)
+            try f.assertImageBuilt(image)
+
+            let containerName = "test-repro-2037-\(UUID().uuidString)"
+            try f.run(["run", "-d", "--name", containerName, image, "sleep", "60"]).check()
+            defer { try? f.run(["rm", "-f", containerName]) }
+
+            try f.assertContainerHasFile(containerName, at: "/run.sh", "/run.sh should exist in image")
+        }
+    }
 }