It looks like Outlook is garbling the reply address.  In the headers it looks like the message is trying to be sent to: naaman.noa1@gmail.com"

<IMCEAMAILTO-naaman+2Enoa1+40gmail+2Ecom@eurprd06.prod.outlook.com

Do you have this address in the contacts for irisy@kpa-group.com? If so, can you try deleting it and seeing if it works properly?

Hi,

Tried to send via the address book - it worked just fine.

Removed the contact from address book - fine as well.

When replying, I get that message (with no more details):

Delivery has failed to these recipients or groups:

naaman.noa1@gmail.com

A problem occurred during the delivery of this message. Please try to resend the message later.

Diagnostic information for administrators:

Generating server:

naaman.noa1@gmail.com

# #MAILTO#

"

That's it, no more details, and it returns the email immediately.

BR.

Are you able to reply to email from other Gmail addresses without a problem?

Do you have any Active Directory contacts for this user in your Office 365?

Also, can you provide the message headers from the email that you received from the gmail address?

You can do this in OWA:

Open the message by double clicking it

Click Message Details at the top (Looks like an open envelope)

Copy and paste the internet mail headers.

Hi Alan,

1.Not getting any other errors when sending to other  gmail users (sometimes for users from other providers).

2.She doesn't have an external account.

3.And the headers for first item: "MIME-Version: 1.0

From: Microsoft Outlook

<MicrosoftExchange329e71ec88ae4615bbc36ab6ce41109e@kpamail.onmicrosoft.com>

To: <irisy@kpa-group.com>

Date: Sun, 22 Jul 2012 08:54:54 +0000

Content-Type: multipart/report; report-type=delivery-status;

boundary="4b98f1ab-1559-446a-a1eb-7389d82d39bb"

X-MS-Exchange-Organization-SCL: -1

Content-Language: en-US

Message-ID: <be4ebf88-e8d1-417b-bd14-377203a0531c@kpamail.onmicrosoft.com>

In-Reply-To: <26F31AAE5B189248B69513EDD7995B0B3722D8@AMXPRD0610MB365.eurprd06.prod.outlook.com>

References: <CAFxbFFWt98c3urs0zez=dLZ_fHCM27KN9nybTaUdGkmY2vS_bg@mail.gmail.com>

<26F31AAE5B189248B69513EDD7995B0B371D4D@AMXPRD0610MB365.eurprd06.prod.outlook.com>

<93E3180410856342A3C3FFD8E76592841E2A4BFD@SBS.radmal.local>

<26F31AAE5B189248B69513EDD7995B0B3722D8@AMXPRD0610MB365.eurprd06.prod.outlook.com>

Thread-Topic: =?iso-8859-8-i?B?7vnr5fjl+g==?=

Thread-Index: AQHNZ9WuQRCesZ+GRkuXqLPYYar+6Jc04s1g////cZCAAB2K8P///98Z

Subject: =?iso-8859-8-i?B?VW5kZWxpdmVyYWJsZTogRlc6IO756+X45fo=?=

X-MS-Exchange-Organization-AuthSource:

AMXPRD0610HT002.eurprd06.prod.outlook.com

X-MS-Exchange-Organization-AuthAs: Internal

X-MS-Exchange-Organization-AuthMechanism: 05

X-MS-Exchange-Organization-AVStamp-Mailbox: MSFTFF;1;0;0 0 0

X-EsetId: F25DD32394900130A71A8C

"

4.For the 'short' error there are no headers, only these details:

Diagnostic information for administrators:

Generating server:

naaman.noa1@gmail.com

# #MAILTO#

BR.

Sorry, I am after the headers for the message that you are replying to.  You say you get an email from Gmail, and the error is when you reply?  I would like to see the headers of this original email from Gmail, not the bounce message.

Alan,

Thx for the fast response.

The original header from sender (@gmail):

Received: from AMXPRD0610HT003.eurprd06.prod.outlook.com (10.255.58.38) by

AMXPRD0610HT002.eurprd06.prod.outlook.com (10.255.58.37) with Microsoft SMTP

Server (TLS) id 14.16.175.8; Sun, 22 Jul 2012 06:46:11 +0000

Received: from mail260-va3-R.bigfish.com (216.32.180.112) by

AMXPRD0610HT003.eurprd06.prod.outlook.com (10.255.58.38) with Microsoft SMTP

Server (TLS) id 14.16.175.8; Sun, 22 Jul 2012 06:46:11 +0000

Received: from mail260-va3 (localhost [127.0.0.1]) by

mail260-va3-R.bigfish.com (Postfix) with ESMTP id 6D274401BB for

<iris@kpa.co.il>; Sun, 22 Jul 2012 06:46:10 +0000 (UTC)

X-Forefront-Antispam-Report: CIP:209.85.214.179;KIP:(null);UIP:(null);IPV:NLI;H:mail-ob0-f179.google.com;RD:mail-ob0-f179.google.com;EFVD:NLI

X-SpamScore: 0

X-BigFish: ps0(z5109h5105hzc89bhc857hzz1202hzzz2fh5fh2a8h668h839h8e3h)

Received-SPF: pass (mail260-va3: domain of gmail.com designates 209.85.214.179 as permitted sender) client-ip=209.85.214.179; envelope-from=naaman.noa1@gmail.com; helo=mail-ob0-f179.google.com ;9.google.com ;

Received: from mail260-va3 (localhost.localdomain [127.0.0.1]) by mail260-va3

(MessageSwitch) id 1342939568684480_19663; Sun, 22 Jul 2012 06:46:08 +0000

(UTC)

Received: from VA3EHSMHS026.bigfish.com (unknown [10.7.14.243]) by

mail260-va3.bigfish.com (Postfix) with ESMTP id A580A5C0048 for

<iris@kpa.co.il>; Sun, 22 Jul 2012 06:46:08 +0000 (UTC)

Received: from mail-ob0-f179.google.com (209.85.214.179) by

VA3EHSMHS026.bigfish.com (10.7.99.36) with Microsoft SMTP Server (TLS) id

14.1.225.23; Sun, 22 Jul 2012 06:46:07 +0000

Received: by obbeh20 with SMTP id eh20so6844222obb.10        for

<iris@kpa.co.il>; Sat, 21 Jul 2012 23:46:06 -0700 (PDT)

DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed;

       d=gmail.com; s=20120113;

       h=mime-version:date:message-id:subject:from:to:content-type;

       bh=AYu7M0rUoBuZW91KnyZSjNZ6fsIHRvCyL7e3k4AhcT8=;

       b=d06oB7uFKHVZ4yjbPGZvK4nGGYb9TL195LxcseWsGnfKTvPv6DMcOzVtFJNiFSCsfF

        rxLY/9pgd4fwBbdwQJxnaq2acK96zzz8ku4jVJCV9DRcvziwDiJaCTTETuwf6RV9xXB9

        Eh/ZAFCpXpI1rQMCkjiXmQF9sb/YA7TYfGS7bOAylBbTHgBxhA5WCBxPhn2eisROX1WC

        wKNyw1mUk08UXGqYrn+4lvd079JPioeFiulfK91b6j+3zUU5FG7CTUkcnN6HBa/F6nDL

        vo7pNAGMWg2hMAVIO01hDTHTbg7vYuAHLPvoEmYCl18V7cSV+2NW/OXua9af3Z7JKN1s

        fGYw==

MIME-Version: 1.0

Received: by 10.182.50.68 with SMTP id a4mr8694622obo.59.1342939566270; Sat,

21 Jul 2012 23:46:06 -0700 (PDT)

Received: by 10.76.128.173 with HTTP; Sat, 21 Jul 2012 23:46:06 -0700 (PDT)

Date: Sun, 22 Jul 2012 09:46:06 +0300

Message-ID: <CAFxbFFWt98c3urs0zez=dLZ_fHCM27KN9nybTaUdGkmY2vS_bg@mail.gmail.com>

Subject: =?UTF-8?B?157Xqdeb15XXqNeV16o=?=

From: noa naaman <naaman.noa1@gmail.com>

To: <iris@kpa.co.il>

Content-Type: multipart/alternative; boundary="f46d04446bbdcd697504c5657b79"

Return-Path: naaman.noa1@gmail.com

X-MS-Exchange-Organization-SCL: 1

X-MS-Exchange-Organization-AVStamp-Mailbox: MSFTFF;1;0;0 0 0

X-MS-Exchange-Organization-AuthSource:

AMXPRD0610HT003.eurprd06.prod.outlook.com

X-MS-Exchange-Organization-AuthAs: Anonymous

X-EsetId: F25DD32394900130A71A8C

The system reply header is EMPTY.

Only the header from above.

Hi ArielK,

Thanks for your contribution on this forum.

Hi Alan,

Thanks for your update. Based on the information you post, I understand that when you reply an email which is sent from Gmail, you receive a NDR "550 5.4.4 ROUTING.NoConnectorForAddressType; unable to route for address type".

Microsoft has released hotfix for this issue and is available to download here,

Office 2010 - support.microsoft.com/.../2597052

Please refer to the information in the link to see if this will help.

Thanks,
Linda Wang

Hi Linda,

The information above refers only to Word (or Office 2010).

My issue also occurs when I reply from OWA (not only from Office on the PC).

Thanks

Hello Arielk,

This is a follow up regarding undeliverable message returns error. Please advise whether this thread can be close. If you have additional questions or concerns feel free to post on the forum.

Best regards,
Roger