diff --git a/packages/artifact/__tests__/upload.test.ts b/packages/artifact/__tests__/upload.test.ts
index d21c78abdf..9f3ce1a38f 100644
--- a/packages/artifact/__tests__/upload.test.ts
+++ b/packages/artifact/__tests__/upload.test.ts
@@ -2,6 +2,10 @@ import * as http from 'http'
 import * as io from '../../io/src/io'
 import * as net from 'net'
 import * as path from 'path'
+import {mocked} from 'ts-jest/utils'
+import {exec, execSync} from 'child_process'
+import {createGunzip} from 'zlib'
+import {promisify} from 'util'
 import {UploadHttpClient} from '../src/internal/upload-http-client'
 import * as core from '@actions/core'
 import {promises as fs} from 'fs'
@@ -174,6 +178,56 @@ describe('Upload Tests', () => {
     expect(uploadResult.uploadSize).toEqual(expectedTotalSize)
   })
 
+  function hasMkfifo(): boolean {
+    try {
+      // make sure we drain the stdout
+      return execSync('which mkfifo').toString().length > 0
+    } catch (e) {
+      return false
+    }
+  }
+  const withMkfifoIt = hasMkfifo() ? it : it.skip
+  withMkfifoIt(
+    'Upload Artifact with content from named pipe - Success',
+    async () => {
+      // create a named pipe 'pipe' with content 'hello pipe'
+      const content = Buffer.from('hello pipe')
+      const pipeFilePath = path.join(root, 'pipe')
+      await promisify(exec)('mkfifo pipe', {cwd: root})
+      // don't want to await here as that would block until read
+      fs.writeFile(pipeFilePath, content)
+
+      const artifactName = 'successful-artifact'
+      const uploadSpecification: UploadSpecification[] = [
+        {
+          absoluteFilePath: pipeFilePath,
+          uploadFilePath: `${artifactName}/pipe`
+        }
+      ]
+
+      const uploadUrl = `${getRuntimeUrl()}_apis/resources/Containers/13`
+      const uploadHttpClient = new UploadHttpClient()
+      const uploadResult = await uploadHttpClient.uploadArtifactToFileContainer(
+        uploadUrl,
+        uploadSpecification
+      )
+
+      // accesses the ReadableStream that was passed into sendStream
+      // eslint-disable-next-line @typescript-eslint/unbound-method
+      const stream = mocked(HttpClient.prototype.sendStream).mock.calls[0][2]
+      expect(stream).not.toBeNull()
+      // decompresses the passed stream
+      const data: Buffer[] = []
+      for await (const chunk of stream.pipe(createGunzip())) {
+        data.push(Buffer.isBuffer(chunk) ? chunk : Buffer.from(chunk as string))
+      }
+      const uploaded = Buffer.concat(data)
+
+      expect(uploadResult.failedItems.length).toEqual(0)
+      expect(uploaded).toEqual(content)
+    }
+  )
+
   it('Upload Artifact - Failed Single File Upload', async () => {
     const uploadSpecification: UploadSpecification[] = [
       {
diff --git a/packages/artifact/src/internal/upload-http-client.ts b/packages/artifact/src/internal/upload-http-client.ts
index e632c8706c..c9aa36502b 100644
--- a/packages/artifact/src/internal/upload-http-client.ts
+++ b/packages/artifact/src/internal/upload-http-client.ts
@@ -219,16 +219,22 @@ export class UploadHttpClient {
     httpClientIndex: number,
     parameters: UploadFileParameters
   ): Promise<UploadFileResult> {
-    const totalFileSize: number = (await stat(parameters.file)).size
+    const fileStat: fs.Stats = await stat(parameters.file)
+    const totalFileSize = fileStat.size
+    // on Windows with mkfifo from MSYS2 stats.isFIFO returns false, so we check if running on Windows node and
+    // if the file has size of 0 to compensate
+    const isFIFO =
+      fileStat.isFIFO() || (process.platform === 'win32' && totalFileSize === 0)
     let offset = 0
     let isUploadSuccessful = true
     let failedChunkSizes = 0
     let uploadFileSize = 0
     let isGzip = true
 
-    // the file that is being uploaded is less than 64k in size, to increase throughput and to minimize disk I/O
+    // the file that is being uploaded is less than 64k in size to increase throughput and to minimize disk I/O
     // for creating a new GZip file, an in-memory buffer is used for compression
-    if (totalFileSize < 65536) {
+    // with named pipes the file size is reported as zero in that case don't read the file in memory
+    if (!isFIFO && totalFileSize < 65536) {
       const buffer = await createGZipFileInBuffer(parameters.file)
 
       //An open stream is needed in the event of a failure and we need to retry. If a NodeJS.ReadableStream is directly passed in,
@@ -287,7 +293,8 @@ export class UploadHttpClient {
       let uploadFilePath = tempFile.path
 
       // compression did not help with size reduction, use the original file for upload and delete the temp GZip file
-      if (totalFileSize < uploadFileSize) {
+      // for named pipes totalFileSize is zero, this assumes compression did help
+      if (!isFIFO && totalFileSize < uploadFileSize) {
         uploadFileSize = totalFileSize
         uploadFilePath = parameters.file
         isGzip = false