Index: tests/Zend/Http/Client/_files/testUploads.php
===================================================================
--- tests/Zend/Http/Client/_files/testUploads.php	(revision 16853)
+++ tests/Zend/Http/Client/_files/testUploads.php	(working copy)
@@ -2,6 +2,12 @@
 
 if (! empty($_FILES)) {
 	foreach ($_FILES as $name => $file) {
-		echo $name . " " . $file['name'] . " " . $file['type'] . " " . $file['size'] . "\n";
+	    if (is_array($file['name'])) {
+	        foreach($file['name'] as $k => $v) {
+                echo "$name $v {$file['type'][$k]} {$file['size'][$k]}\n";
+            }
+	    } else {
+	        echo "$name {$file['name']} {$file['type']} {$file['size']}\n";
+	    }
 	}
 }
\ No newline at end of file
Index: tests/Zend/Http/Client/SocketTest.php
===================================================================
--- tests/Zend/Http/Client/SocketTest.php	(revision 16853)
+++ tests/Zend/Http/Client/SocketTest.php	(working copy)
@@ -778,11 +778,35 @@
     }
 
     /**
+     * Test that one can upload multiple files with the same form name, as an 
+     * array
+     *
+     * @link http://framework.zend.com/issues/browse/ZF-5744
+     */
+    public function testMutipleFilesWithSameFormNameZF5744()
+    {
+        $rawData = 'Some test raw data here...';
+        
+        $this->client->setUri($this->baseuri . 'testUploads.php');
+        
+        $files = array('file1.txt', 'file2.txt', 'someotherfile.foo');
+        
+        $expectedBody = '';
+        foreach($files as $filename) {
+            $this->client->setFileUpload($filename, 'uploadfile[]', $rawData, 'text/plain');
+            $expectedBody .= "uploadfile $filename text/plain " . strlen($rawData) . "\n";
+        }
+        
+        $res = $this->client->request('POST');
+
+        $this->assertEquals($expectedBody, $res->getBody(), 'Response body does not include expected upload parameters');
+    }
+    
+    /**
      * Test that lines that might be evaluated as boolean false do not break
      * the reading prematurely.
      *
      * @see http://framework.zend.com/issues/browse/ZF-4238
-     *
      */
     public function testZF4238FalseLinesInResponse()
     {
Index: library/Zend/Http/Client.php
===================================================================
--- library/Zend/Http/Client.php	(revision 16853)
+++ library/Zend/Http/Client.php	(working copy)
@@ -691,7 +691,12 @@
         // Force enctype to multipart/form-data
         $this->setEncType(self::ENC_FORMDATA);
 
-        $this->files[$formname] = array(basename($filename), $ctype, $data);
+        $this->files[] = array(
+            'formname' => $formname, 
+            'filename' => basename($filename), 
+            'ctype'    => $ctype, 
+            'data'     => $data
+        );
 
         return $this;
     }
@@ -1058,9 +1063,9 @@
                     }
 
                     // Encode files
-                    foreach ($this->files as $name => $file) {
-                        $fhead = array(self::CONTENT_TYPE => $file[1]);
-                        $body .= self::encodeFormData($boundary, $name, $file[2], $file[0], $fhead);
+                    foreach ($this->files as $file) {
+                        $fhead = array(self::CONTENT_TYPE => $file['ctype']);
+                        $body .= self::encodeFormData($boundary, $file['formname'], $file['data'], $file['filename'], $fhead);
                     }
 
                     $body .= "--{$boundary}--\r\n";