Several desktop email clients can be used to connect to Gmail. However, this benefit can come with an unexpected price tag in the form of complex problems. Here's the warning tale of one company's experience using Outlook 2011 with Google Apps. The Gmail web-based interface is one that requires some getting used to - even Google admits that. For those who would rather use a familiar email program instead, there are a number of options; Outlook, Apple Mail and Mozilla Thunderbird (Mozilla is shifting gears away from Thunderbird development, but this client will still continue to work indefinitely).
As it turns out, Gmail and Google Apps accounts do not sync Gmail Contacts and Calendar. I have tried downloading the Google Apps Sync for Microsoft Outlook here but there is no download link or an automatic download.
In fact, any IMAP or POP mail program will work with Google for email, but Outlook for Windows has the best advantage thanks to a program called Google Apps Sync which can handle synchronization of email, calendar, contacts and notes. The purpose of today's article isn't to advise you on how to configure these clients, but rather to discuss some interesting issues we found using this type of setup. If you'd like to pursue this direction. Google Weekly Newsletter See how to get the most out of Google Docs, Google Apps, Chrome, Chrome OS, Google Cloud Platform, and all the other Google products used in business environments. Delivered Fridays Outlook for the Mac Outlook 2011 for the Mac isn't one of the email programs referenced in the above link, nor is it officially supported by Google (there is no Google Apps Sync for the Mac). In some cases non-supported applications will still work fine if you have know-how and luck; in other cases some very unique problems can develop. My company found the latter scenario not long ago.
We found out that some and talking back and forth between Google servers. We did this as follows:. Set up an IMAP account in Outlook 2011 for email. Set up the Mac Address Book application to synchronize with Gmail, then set up Outlook 2011 to sync with the Mac Address Book via Sync Services.
Set up the local iCal calendar application to synchronize with Gmail (the Outlook 2011 calendar cannot communicate with Gmail, unfortunately) Figure A shows a diagram of how this set up worked. Figure A A MacGyverish diagram This meant Jill could use Outlook 2011 for email and contacts while utilizing iCal for her calendar items. In all three instances the data would be copied back and forth between Gmail and her Mac. Note that the Mac Address Book is sort of the highway for contact transmission; it was decided that Jill should update all contacts in Outlook 2011 so they could then be copied to the Mac Address Book, Google, and her iPhone/iPad. After we conducted the migration all seemed well at first. Jill's emails and calendar items were present and available in Outlook 2011 and iCal, respectively.
She had about 5000 contacts, and these existed in the Mac Address Book and Outlook 2011. One happy outcome, right? Cue the scary bass music. Complex problems A few days later Jill contacted me to report she suddenly had over 100,000 contacts! As it turned out, something eerily akin to a was afoot. I found multiple entries of many contacts, and one apparently bad contact in particular; it seemed a corrupt item had spawned itself over and over again. It was hard to tell what the exact issue was.
Maybe the Mac Address Book kept copying those entries to Outlook 2011 or it was sending them up to Google. Possibly Outlook 2011 was duplicating these contacts to the Mac Address Book like an assembly line gone haywire. Most likely, something was sending the bad contacts in BOTH directions, in an exponential algorithm akin to 2x2x2x2x2x2. I cleaned up the duplicate contacts in Jill's Gmail account, using the 'Find and Merge Duplicates' option. This had to be rerun several times, but eventually the 100K contacts were reduced to the original 5000 or so.
I then located the corrupt contacts and removed those, along with a few others that looked questionable. It was then a race against the clock to do the same cleanup work on the Mac in both the Mac Address Book and Outlook 2011, in order to keep the duplicate contacts from flowing back up to Google. I shut off Sync Services in Outlook 2011, which was synchronizing contacts with the Mac Address Book, then unlinked the Google account in the Mac Address Book. It was tough work deleting the duplicates from both programs; there is an option to do so in the Mac Address Book but it was glacially slow and seemed to keep freezing without results (probably due to the sheer number of entries involved). Eventually after consulting some Apple forums I wound up deleting the Mac Address Book database file and recreating it.
Outlook 2011 had no such duplicate removal option; I had to delete all the contacts manually. There is a product called which claims to be able to remove duplicate contacts in Outlook 2011 but we opted not to pursue it for what we hoped would be a one-shot fix. We were back to where we had started, basically; all the known good contacts were at Google and the Mac Address Book program was empty. I restarted contact synchronization between Google and the Mac Address Book. All the contacts came down properly. I restarted Sync Services to get the Mac Address Book contacts into Outlook 2011, and this seemed to work. However, within a day we had the same exact problem as before, and the corrupt contact entry was back like 'You Know Who.'
We went through the duplicate contact removal steps, but this time left Outlook 2011 out of the mix, choosing to use only the Mac Address Book. If the duplicates returned, we'd know this was the source of the issue. Sure enough, they did. What was next?
I ran through the same process as above to remove the duplicates, but left all contact synchronization off. Research indicated a logjam in ownership of this issue. In a nutshell, Google, Microsoft and Apple denied responsibility for any problems using Outlook 2011 with Google.
I'd come across some discussions of this before we started down this road, but since other comments indicated people were able to get this to work we felt it worth pursuing. A different approach We knew Apple Mail could be used instead of Outlook 2011 for email, but email wasn't the problem - that was working fine. Contact synchronization was crucial to Jill as part of her business operations, especially given the frequent changes in these items. Finally I suggested a third party product called which claims to accomplish what we wanted to do.
Instead Jill voiced her decision to move her mail, calendar and contacts over to a dedicated Apple me.com account and use iCloud for the synchronization of all elements. It wasn't so much that she felt Google was inadequate, but she was looking for an 'all in one' solution.
We took care of this, and set up forwarding from her Google account to her me.com account. She was aware of the difficulties maintaining two email addresses, including replies from each, and opted to notify her contacts that her me.com address was her new primary address; any emails forwarded to her from her Google Apps account could be replied to from the me.com account without concern.
In the end you could argue we were spared further incidents via a 'deus ex machina' stroke of luck, since Jill had been seriously considering an all-Apple environment for her technological needs anyhow. Looking back I don't believe the issue was the fault of any one entity, but rather a 'perfect storm.' When trying to get connectivity established between disparate applications and services a grey area exists between the organizations involved. Is it up to Apple to figure out where the issue with the Mac Address Book and Google synchronization?
Was it Microsoft's fault for not providing a way to connect Outlook 2011 to Google via an Exchange link, the same way Outlook for Windows can? Does Google get a slice of the blame for not supporting the Outlook 2011 client or are they to be praised for their wisdom in keeping their hands off the matter? Was the problem caused by the number of Jill's contacts and some issue such as a bad field buried among one of them? These are questions that could be debated endlessly. This was a good lesson of the necessity to simplify as much as possible, to eliminate as many variables and potential leaks in the communication pipes. Ultimately we didn't find a solution, but we found a workaround, and keeping the wheels of the business turning was the ultimate goal.
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Also of significance, this app syncs contact groups with Google. For instance, you may have organized your Gmail contacts into groups such as 'friends,' 'family,' and 'coworkers.' After syncing, your Mac groups will match your Gmail groups. With the customizability that this app provides, it can be used in a number of creative ways. For example, you can backup your Mac contacts to Gmail, you can sync iCloud or Exchange contacts with Gmail, or you can perform syncs in one direction only (such as Gmail to Mac). Davidatswans2, Where has this app been all my life??? Perfectd for iPhones!!
I’ve now been using this app for almost two months. If you use an email app tied to Google but keep your contacts in Apple’s Contacts app, it is essential for them to sync, since new or revised emails addresses that you load into your Apple Contacts are fetched by your iPhone from Gmail, not from the Apple Contacts. This app makes this constant self-syncing a piece of cake. Be sure to backup your Contacts before using this in case you screw up (I did backup but didn’t screw up), but you’ll be very pleased with the results.
It syncs everything in your Apple Contacts including your notes, addresses, phone numbers, emails, etc. I couldn’t be happier!! Davidatswans2, Where has this app been all my life???
Perfectd for iPhones!! I’ve now been using this app for almost two months. If you use an email app tied to Google but keep your contacts in Apple’s Contacts app, it is essential for them to sync, since new or revised emails addresses that you load into your Apple Contacts are fetched by your iPhone from Gmail, not from the Apple Contacts. This app makes this constant self-syncing a piece of cake. Be sure to backup your Contacts before using this in case you screw up (I did backup but didn’t screw up), but you’ll be very pleased with the results.
It syncs everything in your Apple Contacts including your notes, addresses, phone numbers, emails, etc. I couldn’t be happier!! Reidg, This app corrects a macOS bug!
At some point in the past year my Google contacts would no longer appear on eithe of my two Macs. I was keeping all of my contacts only in Google so this presented a problem with Messages and other Contacts dependant apps. I decided to try this app and now all of my Google contacts and groups are successfully syncing with my iCloud contacts. I did remove the Google Contacts connection from my settings to avoid duplicates. Keep in mind, to sync more than 40 contacts you’ll need to upgrade for $5. Well worth it in my opinion. Reidg, This app corrects a macOS bug!
At some point in the past year my Google contacts would no longer appear on eithe of my two Macs. I was keeping all of my contacts only in Google so this presented a problem with Messages and other Contacts dependant apps.
I decided to try this app and now all of my Google contacts and groups are successfully syncing with my iCloud contacts. I did remove the Google Contacts connection from my settings to avoid duplicates. Keep in mind, to sync more than 40 contacts you’ll need to upgrade for $5.
Well worth it in my opinion. Great app and cust support, Excellent app! This is an excellent app, and worthy of the life saving label. I have over 3800 contacts with multiple entries and decide to move away from iCloud. I bought this app after doing my research and looking at several competing apps. I cannot say enouht about the tech support above and beyond the call of duty. I sync 6 devices that include 2 MacBook Pros, iPhone, iPad, iMac and a Google Pixelbook.
Tech support was unfailingly patient with my repeated requests and knew the questions to ask. Cannot recommend it enough. Great app and cust support, Excellent app!
This is an excellent app, and worthy of the life saving label. I have over 3800 contacts with multiple entries and decide to move away from iCloud. I bought this app after doing my research and looking at several competing apps. I cannot say enouht about the tech support above and beyond the call of duty. I sync 6 devices that include 2 MacBook Pros, iPhone, iPad, iMac and a Google Pixelbook. Tech support was unfailingly patient with my repeated requests and knew the questions to ask.
Cannot recommend it enough.