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kzabbott
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Atachment from Eudora 6.2.4 for MAC OSX won't open in Outlook for Exchange 2003

I am trying to figure out why attachments from Eudora 6.2.4  for MAC OSX won't open in Outlook for Exchange 2003.

We have a Microsoft Office Word file, originally created in Word 2003 for Windows, which was sent to a Macintosh OSX user for review and markup.  That file was sent back via Eudora 6.2.4, and when we tried to open the file on the PC the the "File Conversion" dialogue box appears.

We tried the following combinations, with the following results which have provided us with at least one "workaround", but I am still interested in understanding/resolving the actual problem.

I
Sent using Eudora 6.2.4 on a iMac running OS 10.4.11
encoding is AppleDouble ("MIME")
"Always include Macintosh information" is checked
uncompressed Word file
Would not open from Outlook 2003 (Exchange 2003 account) - got the File Conversion box.

II
Sent using Eudora 6.2.4 on a iMac running OS 10.4.11
encoding is AppleDouble ("MIME")
"Always include Macintosh information" is NOT checked
uncompressed Word file
Would not open from Outlook 2003 (Exchange 2003 account) - got the File Conversion box.

III
Sent using Apple Mail 2.1.3 on a iMac running OS 10.4.11
"Send Windows Friendly Attachments" is selected
uncompressed Word file
File opened without problem from Outlook 2003 (Exchange 2003 account)

IV
Sent using Eudora 6.2.4 on a iMac running OS 10.4.11
encoding is AppleDouble ("MIME")
"Always include Macintosh information" is checked
uncompressed Word file
Sent to a POP3 account, the file opened without problem on the PC, and when forwarded from the POP3 account to the Outlook/Exchange account it also opened without problem

V.
Sent using Eudora 6.2.4 on a iMac running OS 10.4.11
encoding is AppleDouble ("MIME")
"Always include Macintosh information" is NOT checked
uncompressed Word file
Sent to GMail account, the file opened without problem on the PC, and when forwarded from the GMail account to the Outlook/Exchange account it also opened without problem

VI
Sent using Eudora 6.2.4 on a iMac running OS 10.4.11
encoding is AppleDouble ("MIME")
"Always include Macintosh information" is checked
uncompressed Word file
Would not open from Outlook Web Access (OWA) on a Mac Mini running OS 10.4.11.

VII
Sent using Eudora 6.2.4 on a iMac running OS 10.4.11
encoding is AppleDouble ("MIME")
"Always include Macintosh information" is checked
uncompressed Word file
Opened with out problem from Entrouage 2004 (configured with Exchange 2003 account)  on the MAC Mini running OS 10.4.11.

VIII
Sent using Eudora 6.2.4 on a iMac running OS 10.4.11
Encoding "AppleDouble" (MIME)
Compressed/Zipped file - opens without problem from any Email program on PC or Macintosh after being unzipped.

The question seems to be:  What is happening with Outlook 2003, SP3 for Exchange 2003, or with Outlook Web Access (whether on the PC or on the MAC) that makes the file unreadable on the PC?



Email ClientsOutlookMac OS X

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Last Comment
kzabbott

8/22/2022 - Mon
apache09

In outlook, can you right click on the attachment and Save As?
When you do this, what extension is the file being Saved As?

If you save it locally, can you then go and open it using Word?
kzabbott

ASKER
It has a .doc extension, and no, I can not open it if I save it locally; it makes no difference whether I double-click or whether I try to open the file from within Word.

To add to the issue, since I posted this question, I have determined that if the file is sent from Eudora for MAC OSX using UUENCODE instead of AppleDouble, it works fine.   So this narrows it down to be an issue with Exchange 2003 or Outlook 2003 interpreting the AppleDouble encoding (even though Entourage 2004 for MAC can interpret it correctly).  

I'm wondering if there is a tweak or fix or Outlook 2003 for Windows or Exchange 2003 so they will properly recognize AppleDouble encoding.
apache09

What Office Service Pack is installed on this PC with Outlook 2003?
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kzabbott

ASKER
Apache09 - that's office SP3  - sorry; thought I had stated that.
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apache09

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apache09

apache09

Sorry didnt notice this:

V.
Sent using Eudora 6.2.4 on a iMac running OS 10.4.11
encoding is AppleDouble ("MIME")
"Always include Macintosh information" is NOT checked
uncompressed Word file
Sent to GMail account, the file opened without problem on the PC, and when forwarded from the GMail account to the Outlook/Exchange account it also opened without problem


This should be the proper format to send the email via MAC. If this email is sent directly to Outlook, rather than being forwarded from Gmail, does this work?
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apache09

* Perhaps the answer is stated in II
apache09

When sending from Eudora, is it possible to try to send in different email formats such as Plain Text or HTML?
How is the file being attached?

Here is an EE discussion. Not exactly the same problem but may help:
https://www.experts-exchange.com/questions/22857858/Mac-Mail-sending-email-to-Outlook-on-PC-problems.html
apache09

Something else to try?

In Outlook, Tools>Options>Security Tab>Download Pictures> Change Automatic Download Options.
Try un-checking "Dont download pictures or other content automatically in HTML e-mail"
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kzabbott

ASKER
I'm closing this and givng you the points as you are the only one who responded (and I thank you for that!).  Don't really have the answer, but at least we can get the files in usable format if the sender will send in UUEncode instead of AppleDouble.  I'd just like to find some way for Exchange 2003/Outlook 2003 to recognize AppleDouble, but oh well...

Thanks again!