Need An E-Mail Client Strategy...Please Help...

I need an e-mail strategy…



I will start by providing some background information…

1. I have been a Windows user for the pas 20 years and have -- at least for personal use -- made the move from Windows to OS X.


2. I use Microsoft Outlook 2010 for Windows for work e-mails that is connected to a Microsoft Exchange Server. I save all of my e-mails on my hard drive as *.MSG files [long story but suffice it to say that this is necessary].


3. In transitioning from Windows to OS X I installed Parallels Version 8 and Microsoft Outlook 2010 for Windows. This solution works perfectly for my work e-mails.


4. In transitioning from Windows to OS X I took he opportunity to separate my personal e-mails and my work e-mails by creating and using an @icloud.com e-mail account for all my personal e-mails…the next step in the setup process was to setup my @icloud.com e-mail account in Outlook 2010 for Windows which was simple and straight forward…the results -- on the other hand -- are terrible for a number of reasons including the following:

a. The @icloud.com folders DRAFT / SENT / TRASH / do not sync with the Outlook 2010 for Windows folders of DRAFT / SENT / DELETE which means that there can or is the need to manually keep the mail clients [i.e. @icloud.com web interface and Microsoft Outlook 2010 for Windows] in sync.

b. There is a problem sending e-mails…an @icloud.com e-mail sent from the @icloud.com web interface does not -- for the reason noted in a. above -- appear in Outlook 2010 for Windows which means that I have no way of saving the resulting e-mail as an *.MSG file unless I also include my @icloud.com e-mail address as a recipient [which is dumb]…an @icloud.com e-mail sent from Outlook 2010 for Windows does not -- though this could be an Exchange issue that I need to discuss with my work IT Department -- appear in Outlook 2010 for Windows which means that I once gain have no way of saving the resulting e-mail as an *.MSG file unless I also include my @icloud.com e-mail address as a recipient [which is dumb].

c. There is a problem with my BlackBerry…if I add my @icloud.com e-mail address to my BlackBerry then I can not even send e-mails from my @icloud.com e-mail address within Outlook 2010 for Windows [i.e. the e-mails hang and get stuck in my Outbox]…If I remove my @icloud.com e-mail address from my BlackBerry then e-mails from my @icloud.com e-mail address sent within Outlook 2010 fro Windows are successfully transmitted.



I would like an e-mail strategy that satisfies the following:

1. One client…I need one client for both my personal e-mails and my work e-mails…though I would prefer an OS X client I am comfortable with a Windows client [as noted by my current usage of Parallels and Microsoft Outlook 2010 for Windows].


2. Read / save e-mails in *.MSG format…I need the ability to read *.MSG files with all attachments and formatting maintained because without this capability I will not be able to access historical e-mails [and, there are a lot of them]…I need the ability to save new e-mails in *.MSG format for purposes of i) compatibility with work [and my work Windows laptop] and ii) safety / security in the event that I need to move back to a Windows environment.


3. Syncing capability that works…the client must sync fully with Outlook 2010 for Windows for my work e-mails so that I do not have to manually keep things in sync and, similarly, the client must sync fully with the @icloud.com web interface so that I do not have to manually keep things in sync.


4. Though not as critical as the preceding items, the ability to access / read e-mails without starting Parallels and then starting Outlook…this -- I think -- is self-explanatory.


5. Etc. [as a placeholder for other critical items that escape me at the minute].




With the above in mind i see two possible strategies:

1. Move to another mail client [possibly even the Mail client included in OS X]…the issue here is that i) I know nothing about OS X Mail and ii) I know nothing about other mail clients as I have used nothing but Microsoft Outlook for Windows for the last 15+ years…I suppose / think that OS X Mail might be a solution subject to the following:

a. Can OS X Mail [or, another client] be made to work with Microsoft Outlook 2010 for Windows noting I have access to Outlook 2010 for Windows via either i) a Microsoft Exchange Proxy Server (i.e. https:// URL) or ii) when in the office or connected to the office via VPN a Microsoft Exchange Server. The point being that I do not have or know IMAP or SMTP addresses.

b. Can OS X Mail individual e-mails be saved as *.EML files because I think that Outlook 2010 for Windows can open / read *.EML files which would provide the necessary backward compatibility / safety . And,if yes, then how is this done?

c. Can someone confirm that Microsoft Outlook 2010 for Windows can natively read *.EML files.

And,if the answer to all of the above is yes please provide me with instructions [or, alternatively, a URL] as to how to set this up as this is all new territory to me.


2. Stick with the current setup -- which is less than ideal -- with the addition of a *.MSG viewer such as MSGViewer [see http://www.element26.net/products/shop/outlook-msg-viewer/?gclid=CJbayLW2vrQCFeZDMgod-EUAIQ ] which will address all my needs OTHER THAN 3 above which is admittedly important.


WIth much thanks for both reading this post as well as providing me with assistance.


Joel

nielsrasmus said:

Hi Joel,

Click to expand...

Hi...appreciate your response but believe that there is some confusion so here goes...

nielsrasmus said:

I think your troubles are boiled down to the issues you describes above.

In order to make your email client to sync properly you must have the credentials for your company's mail server. If you don't have it, forget it!

Click to expand...

I disagree in that the issue is *not* that I can not get things to sync it is rather that they do not sync nicely...let me explain:

1. @work.com e-mail is not an issue as Outlook 2010 for Windows ("Outlook") syncs perfectly.

2. @icloud.com e-mail address is a problem...Outlook -- when setup to be client / front end for an @icloud.com e-mail address -- does not sync the icloud DRAFT | SENT | TRASH folders with its (i.e. Outlook's) DRAFT | SENT | DELETE folders...Outlook rather creates "user" folders called DRAFT | SENT | DELETE which also appear in the @icloud.com e-mail "web access page".

Although I am far from an e-mail expert I suspect that this is an Outlook design / usage issue...I say this because I do have the @icloud.com IMAP and SMTP server adresses.

nielsrasmus said:

I too have windows at work and OSX at home. And these accounts are separated. But as I understand you want to connect both in a single client, which could be very troublesome in the long term.

Click to expand...

I would appreciate you expanding on this as I do not see understand why it could be troublesome to have once client (i.e. application such as Mail, Outlook, etc.) access both my work and personal e-mail...in point of fact, this is exactly what takes place on my iPad.

nielsrasmus said:

When I took the trip to the Mac platform i had all my emails on Gmail. What I did was to connect Gmail as IMAP in mail.app and the copied it all from Gmail to mail.app. Then I changed my email address to @me.com.

You could make a "rule" that forwards your private email to your personal @icloud.com address, otherwise you can forward it manually. But that won't keep/save your .msg files on the hard drive without the hassle of moving them manually

Click to expand...

Luckily I had the foresight to cover this off as this is not an issue as I already have all my personal e-mails separated...

nielsrasmus said:

You also want your private messages being kept in .msg format perhaps because you are not sure if you want to return to windows later on?

Well, actually you can purchase Outlook for mac, in case you didn't know: http://www.microsoft.com/mac/outlook.

Click to expand...

There are multiple reasons as to why I want my personal e-mails kept in a *.MSG format...they include the desire to have one application to deal with both new and old e-mails, possibly of returning to windows, etc.

Windows for Mac is not a solution for a number of reasons not the least of wich being in does NOT use the *.MSG format but rather the *.EML format.

nielsrasmus said:

Beware of the different mail formats because some may be converted to plain text and your formatting and attachments are then gone to the eternal bitfields

This describes shortly the most common mail formats: http://en.wikipedia.org/wiki/E-mail#Filename_extensions

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Yes, this is a problem that I am trying to avoid and, once again, thanks for the input!

***

The item that I would very much like a response to which could / would point me in the right directions is the portion of my original posting which reads...

1. Move to another mail client [possibly even the Mail client included in OS X]…the issue here is that i) I know nothing about OS X Mail and ii) I know nothing about other mail clients as I have used nothing but Microsoft Outlook for Windows for the last 15+ years…I suppose / think that OS X Mail might be a solution subject to the following:

a. Can OS X Mail [or, another client] be made to work with Microsoft Outlook 2010 for Windows noting I have access to Outlook 2010 for Windows via either i) a Microsoft Exchange Proxy Server (i.e. https:// URL) or ii) when in the office or connected to the office via VPN a Microsoft Exchange Server. The point being that I do not have or know IMAP or SMTP addresses.

b. Can OS X Mail individual e-mails be saved as *.EML files because I think that Outlook 2010 for Windows can open / read *.EML files which would provide the necessary backward compatibility / safety . And,if yes, then how is this done?

c. Can someone confirm that Microsoft Outlook 2010 for Windows can natively read *.EML files.

And,if the answer to all of the above is yes please provide me with instructions [or, alternatively, a URL] as to how to set this up as this is all new territory to me.

Hopefully someone out there will be able to chime in on this as I am currently extremely frustrated..

Thanks,


Joel

James Craner said:

Ok first thing - iCloud is a IMAP email system, which means that any changes that you make should sync through to all devices, provided they are saved on the server. Most clients give you the option to say if you want sent messages stored on the server. If you are sending emails in the iCloud web interface and they are not syncing through to Outlook, check the preference settings in the iCloud Web interface. To do this click the cog wheel in the upper right, and choose preferences. In the General tab, make sure that sent emails are saved - see the screenshot below.

View attachment 386638

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Appreciate the response...

To clarify any and all misunderstanding the problem was form the opposite direction in that @icloud.com e-mails that I sent from within Outlook simply vanished and appeared nowhere in either the iCloud web interface or Outlook and that was with the iCloud web interface preferences being set up as you suggest...

The issue -- at least for this one -- seems to be that there are no such "working" preferences in Outlook and even were they to exist they would not be of much help because -- as noted in the OP -- the SENT folders do not sync.

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hallux said:

A word of note, and possibly why you're having trouble connecting to your work mail server from your OS X mail client, I believe Lion introduced a requirement of Exchange 2010 on the server side in order for the mail client to connect (unless the Exchange admin installed some add-in on your Exchange 2007 server). Outlook 2011 will also have a similar requirement.

To connect to Exchange using Mail, the administrator must have EWS (Exchange Web Services) configured. This may be the part that I mention above, I just know that when we introduced Macs at work almost 2 years ago we had to migrate people that were getting one to an Exchange 2010 environment for Outlook 2011 to connect.

Click to expand...

Appreciate the response...

I was asking -- in the original post -- whether or not it was possible to use OS X Mail as a mail client for connecting to Exchange...

With a little trial and error I was successful in getting the two to speak...more on this below...

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glenthompson said:

Before moving to OS X I used Outlook on Windows and used the same for work and personal email. I created different profiles in Outlook, one for work and one for personal. The work profile connected to the exchange server and the personal profile connected to my ISP. It might be a possible solution.

Click to expand...

Appreciate the post...

I have tried this as well but it does not solve the issue / problem...the two profiles do connect separately but the Exchange / iCloud folder syncing is still not working...

More on this below...

Current Strategy...What Do You Think...

The first option is to use OS X Mail as a mail client for both my @icloud.com e-mail address and my @work.com e-mail address. The following is noted in respect of this strategy:

1. The pros include:

a. All new e-mails can be saved in the *.EML format. This is not an issue in the event of i) a return to Outlook 2010 as an e-mail client ii) a return to Windows or iii) other like event as Outlook 2010 can read *.EML files.

b. Effective / good syncing in respect of my @icloud.com e-mail address between my BlackBerry, @icloud.com web interface and Outlook which includes:

c. Native application meaning:



2. The cons include:

a. All existing e-mails that are saved in the *.MSG format need to be read through the use of MSG Viewer. This is an issue – subject to speaking with the developer – as attachments (i.e. PDF files, Word files, etc.) do not appear.

b. The inability to flag new e-mails for DELIVERY RECEIPT and READ RECEIPT.

c. The text editing capabilities / features for new e-mails are far worse. These include the lack of availability / use of a ruler, the lack of availability / use of different paste options, the poor demarcation of new e-mails, etc.



The second option is to use Windows Outlook 2010 for both my @icloud.com e-mail address and my @work.com e-mail address. The following is noted in respect of this strategy:

1. The pros include:

a. All existing e-mails that are saved in *.MSG format can be read.

b. All new e-mails can be saved in *.MSG format.

c. The ability to flag new e-mails for DELIVERY RECEIPT and READ RECEIPT.

d. The text editing capabilities / features for new e-mails are far greater. These include the availability / use of a ruler, the availability / use of different paste options, the demarcation of new e-mails, etc.



2. The cons include:

a. Ineffective / poor syncing in respect of my @icloud.com e-mail address between my BlackBerry, @icloud.com web interface and Outlook which includes:



b. The need to start Parallels in order to start Outlook.





Based on the above I believe that the preferred strategy – particularly in the event the above described issue in respect of MSGViewer can be resolved – is to use OS X Mail as the mail client.

As always, I am interested in the input and thoughts of others.

Thanks,


Joel

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James Craner said:

Ok next issue is getting your Draft / Sent / Trash folders to sync correctly

To access the iCloud special folders: Sent, Archive, Drafts, Junk or Trash in Outlook 2010 (which initially creates its own version of these folders): Right click the Mailbox, select “IMAP Folders” and then “subscribe” to the folders you want to see.

Following this you can modify Outlook to use the iCloud folders for Sent and Trash instead of newly created default: Go to Email Accounts, Change, More settings and make the changes in the “Sent Items” and “Deleted Items” tabs. Noting that Outlook it sees Trash as “Deleted Messages” and Sent as “Sent Messages” – but they are the same folders.

Click to expand...

Appreciate the response...

Ooops and embarassingly I missed this post this morning...I will give it a go and see how / whether this changes my just posted strategy...

James Craner said:

Well in that case it looks like all your iCloud email problems stem from the fact that folders are not syncing, Hopefully if you follow my advice in the 2nd post I made - that can be fixed.

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Correct about the problem flowing from the lack of synchronization...

I will -- as noted above -- try your solution with the hope that it will work...

James Craner said:

Which version of windows are you using ? I presume it is XP as Apple does not officially support it, although you should get Outlook to work fine with some tweaking.

Click to expand...

Windows 7...

We Are Close....

James Craner said:

Ok next issue is getting your Draft / Sent / Trash folders to sync correctly

To access the iCloud special folders: Sent, Archive, Drafts, Junk or Trash in Outlook 2010 (which initially creates its own version of these folders): Right click the Mailbox, select “IMAP Folders” and then “subscribe” to the folders you want to see.

Following this you can modify Outlook to use the iCloud folders for Sent and Trash instead of newly created default: Go to Email Accounts, Change, More settings and make the changes in the “Sent Items” and “Deleted Items” tabs. Noting that Outlook it sees Trash as “Deleted Messages” and Sent as “Sent Messages” – but they are the same folders.

Click to expand...

James:

Appreciate the help greatly...

As of the most recent testing we are close but quite there...here is the status with respect to iCloud e-mails:

1. E-mails managed / sent from either the iCloud web interface or the OS X Mail client do show / sync perfectly in the Outlook client...this is fantastic.

2. E-mails managed [i.e. moved between folders] from the Outlook client client do show / sync perfectly in the iCloud web interface and the OS X Mail client...this is fantastic.


3. E-mails sent from the Outlook client *do not* appear in any of the iCloud clients / interfaces [i.e. iCloud web interface, OS X Mail client or Outlook] despite the fact that Outlook is being told to save sent messages to the SENT MESSAGES folder [as well as store them on the server] and move deleted message to the DELETED MESSAGES folder [***NOTE THAT THESE SYNC PROPERLY WITH MESSAGES SENT FROM EITHER THE WEB INTERFACE OR THE OS X CLIENT]

To the extent you can dig into the "knowledge well" one more time to get e-mails sent from Outlook appear in all "clients" we will be good to go.

With much thanks,


Joel

James Craner said:

Ok Now I know that you are on Windows 7, the easiest way to set up iCloud email is to use the iCloud control panel for Windows.

I suggest that you first backup your email, and delete the existing iCloud account in Outlook using these instructions. Your emails will still be on the iCloud servers so removing the account in Outlook should not cause you to lose any data, but backup just in case.

Remove an email account in Outlook

Click the File tab.

Under Account Information, click Account Settings, and then click Account Settings.

Select the email account that you want to remove, and then click Remove.
To confirm removal of the account, click Yes.

Then download the iCloud control panel

and follow the instructions on the site linked above. If you don't want the other iCloud stuff setup - just select email in the iCloud options.

Click to expand...

James:

Again, appreciate the response...

As far as your solution is concerned but before doing so -- as I am having problems loading the web page -- can you please confirm that the iCloud control panel and related process will result in my @iCloud.com e-mail being added to Outlook as this -- for the reasons explained above -- is a critical part of my needs..,

Once again, thanks so much,

Joel

James Craner said:

Ok Now I know that you are on Windows 7, the easiest way to set up iCloud email is to use the iCloud control panel for Windows.

I suggest that you first backup your email, and delete the existing iCloud account in Outlook using these instructions. Your emails will still be on the iCloud servers so removing the account in Outlook should not cause you to lose any data, but backup just in case.

Remove an email account in Outlook

Click the File tab.

Under Account Information, click Account Settings, and then click Account Settings.

Select the email account that you want to remove, and then click Remove.
To confirm removal of the account, click Yes.

Then download the iCloud control panel

and follow the instructions on the site linked above. If you don't want the other iCloud stuff setup - just select email in the iCloud options.

Click to expand...

James:

I will post / write a more detailed follow up later -- will try for late tonight but will likely be very early tomorrow morning -- as I have both i) tried your suggested approach [which does nicely integrate with Outlook] and ii) with the insight learnt, happened upon an even better method that I will layout in detail for others who may go down this road.

I would likely a response to one more item which would assist / fill in the last remaining blank...the issue / items is whether or not the Outlook Options local to each profile or global to all profiles...

With much thanks,


Joel

James Craner said:

Joel,

Looks like you got the link to the iCloud control panel to work then, as it worked ok for me.

Click to expand...

Correct...

James Craner said:

I was pretty sure your problem was the was the way your iCloud account in Outlook was originally configured.

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Correct...the second problem was that I was not sufficiently familiar with Outlook's configuration options for IMAP accounts...with the added knowledge that you posted the solution was readily at hand...

James Craner said:

The iCloud control panel looked like the easiest way to solve this, as different people appear to use different settings for Apple's servers. Anyway would be interested to find out how it went and your current thoughts.

Regards

James

Click to expand...

Correct...the iCloud WIndows Applet is the easiest but -- at least to me -- not the best...

I am putting the finishing touches on a more detailed explanation in Word and will post it shortly...

Thanks for everything as I would have never figured this out without your help...

Joel

We Are Almost There..Which Is Preferred...

James Craner said:

Anyway would be interested to find out how it went and your current thoughts.

Regards

James

Click to expand...

James and to anyone else who may find this helpful...

First, allow me to thank you for posting in this thread as your posts – and, in particular, those related to configuring IMAP e-mail folders within Outlook – were critical in providing me with the roadmap for successfully configuring my @icloud.com e-mail account within Outlook 2010 for Windows (“Outlook”).


Second, though I did successfully install and setup the iCloud for Windows applet I have decided not to use it for a number of reasons including:






Third, with the above in mind, the approach I followed is i) create a separate Outlook profile called iCloud ii) manage the @ icloud.com e-mail folders per your e-mail (i.e. added the @icloud.com folders TRASH | DRAFT | SENT *and* deleted the Outlook folders DELETE | DRAFT | SENT) and iii) setup Outlook such that sent e-mails are automatically saved to the SENT folder** (which, per ii) is the @icloud.com SENT folder). This setup woks perfectly in that the @icloud.com TRASH | DRAFT | SENT folders from the @icloud.com web interface, the OS X Mail client and Outlook all sync perfectly.


This leaves me with two functional mail clients – OS X Mail and Outlook 2010 for Windows – which meet my primary needs which include i) one mail client for both my personal e-mail and work e-mail ii) the ability to read and save -mails in the *.MSG format and iii) the ability to reliably and successfully sync my @icloud.com e-mail folders.


With that there are still differences (i.e. pros and cons) between the options:
























Your thoughts – based on the above – as to which mail client – OS X Mail or Outlook 2010 for Windows – is the preferred mail client would be greatly appreciated.

Joel


**The reason that I asked in a previous post whether the Outlook Options are local to each profile or global to all profiles is because my work profile which i) excludes the saving of sent e-mails in the sent folder and ii) was the reason that @icloud.com sent mails were not being saved. Without knowing whether the Outlook Option are local or global I created a rule (in my iCloud profile but NOT in my work profile) which forces sent e-mails to be saved.

While I continue to search for the answer on the internet, do you know whether the Outlook Options are local to each profile or global to all profiles?

takeshi74 said:

You could run Parallels in coherence mode (though you're technically still starting Parallels to run Outlook 2010).

Click to expand...

Appreciate the response and agree with you in that I could run Outlook 2010 in Coherence mode...

I have tired / used Parallels in coherence mode and prefer not to use it in coherence for a number of reasons including the fact that I am a minimalist and do not like the "clutter" than Parallels adds to my desktop / dock / etc. when used in coherence mode.

Parallels is a wonderful product that despite being extremely configurable does not address / consider this issue...though I am but a voice of one, my ideal Parallels setup would be coherence mode without all of the cross-application accessability.

Thanks for your suggestion,


Joel

James Craner said:

Hi Joel,

I am happy that you have got your iCloud account to work and that I was able to help. My goal was to get iCloud working for you in Outlook so that you could decide what works best for you. I can't really help with your decision as it looks like you have a specific list of requirements, that to be honest only you can make the call on what is important to you. You appear to have a longer list of Cons on OS X Mail, and if most of your Mail comes from Exchange, then Outlook may be the better option.

When I used to work for a big US Company I used Entourage (used to be Microsoft's Mail offering in Mac Office, before they switched to Outlook in 2011) to manage my exchange based Work email, and I used OS X Mail for personal mail.

Click to expand...

Agree and understand what you are saying...I will likely follow a bit of a hybrid approach in that I will use Mail for all my personal e-mails , use Mail to monitor my work e-mails through the Message Centre and, use Outlook to process work e-mails...I will see how this goes and then go from there.

James Craner said:

Now I just use Mac Mail for everything as I have spent a lot of time getting my Mail workflow right for me, using GTD principles, I try to read my emails only once and they stay in my inbox for less than a day, before they are 'processed'.

Click to expand...

Interesting read as I have been doing this essentially my entire working life in that I rarely go to sleep with any e-mails in my inbox and, to the extent there are any, they are there to remind me to call the sender the next day.

In point of fact this is one of the reasons that I save my e-mail is *.MSG format because it creates a discipline to act on your e-mails because they need to be moved.


One last item for -- any idea on the Outlook Option settings as to whether they are local or global?


Thanks you have been a huge help!


Joel

James Craner said:

Hi Joel - unfortunately I am not sure of the answer to that one, although I would imagine that the settings are local to the profile, rather than global, but that is just an educated guess as it does not make sense to set an individuals personal email settings across different Windows user profiles on the same machine.

Click to expand...

James:

Appreciate the response...I am following up this item in the Microsoft Community Forum and it appears that other than i) Account Settings and ii) View Settings the parameters are indeed global...I will post the final answer here for those interested...


Joel

For those interested and following this thread you may be interested to note that I spoke to the developer of MSGViewer this evening and he assured me that the non-trial version of his application will display *.MSG file attachments.

I will be purchasing the application tomorrow -- it costs $10 -- as he agreed to refund my money in the event that it does no work [i.e. does not display attachments].

In the event that it does work then there will two functional mail clients that met my list of requirements...though I am a long times Windows user I am seriously considering migrating to OS X Mail despite its more limited capabilities -- as documented above -- as I like the idea of using a natice application.

More to follow....


Joel

I have since purchased a copy of MSGViewer and confirm that it works as advertised with all attachments being available / visible...the only nit is that attachments do not open when double clicked on but are rather downloaded to the Download folder..

I think the strategy that I will deploy now that I have two functional clients is to use both clients...that is:

1. I will use OS X Mail to i) monitor and triage incoming e-mails ii) draft short responses to incoming e-mails and iii) access / view existing e-mails [with MSGViewer] as I prefer its interface and simplicity over Outlook; and

2. I will use Outlook to draft detailed responses that need greater formatting capability or read / receipt capability.

Since everything is syncing properly this should be extremely efficient and workable.

With much thanks to all who helped me get here,


Joel