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September 8, 2009

Snow Leopard/MS Entourage/Address Book NIGHTMARE

Hi Everyone,

Bear with me. I'm posting this at my blog, in a note at Facebook, in the tech forum at Apple's site, and that means it's going to be a nice, long read to get everyone up to speed in case there's a kind soul out there who can help with this ridiculousity. Keith is also taking a print-out of this whole thing to the Genius Bar tomorrow. Our last hope.

I'll be copying and pasting some info from previous accounts, in case the back-story is helpful. First, a post from a Yahoo Group I manage, where I was trying to get suggestions for contacts management software when Entourage was having issues of data loss (May 2009). It seems we were able to fix the problem with some good old-fashioned database repair and restore. That was all well and good... 'til Snow Leopard came along. Right now, I'd like to find that little kitty and kick it in the crotch.

Happy reading and thanks in advance for ANY help you might be able to provide!


May 21, 2009:

Hi HHHers,

Okay, so I need some really wonderful contacts-management software. Here's my criteria:

- runs on Mac
- syncs b/w iPhone and Microsoft Entourage
- manages over 11K contact files (and growing)
- doesn't duplicate files, re-label fields, drop category designation, or lose contact history when synced

Basically, I've been using Microsoft Entourage since 1999. I have, organically, built my contact database using the Entourage "address book" feature for a decade. (This does NOT include contacts via my column, the showcase, or any other contact made via one of my Gmail addresses. I let Gmail deal with those, as they're "low frequency of contact" compared to the files in my master database. No, I do not currently run a commercial mailing list, nor am I looking to do so. So, I'm not looking for "Constant Contact" or something like that. I do *have* a mailing list via Yahoo Group and let it manage that list. This is JUST my contact list of casting colleagues, agents, managers, publicists, actors, writers, directors, producers, showrunners, etc. Yes. Really.) Every contact is color-coded by category. Entourage links our history of correspondence (this is spotty at best). I have cool "rules" set up in Entourage to route mail--based on contact category and mail history--into appropriate inboxes, prioritized accordingly.

(I'm showing y'all a bit of the "behind the curtain" on how I'm so productive b/c it's relevant to the tech question I have. I have lots of "helps" to knowing how to prioritize, when too much has come in and I only have a few moments to deal with things.)

So, as I've migrated my handheld devices from Palm (2000) to Visor (2002) to Treo (2004) to Blackberry (2006) to iPhone (2007), it's largely been because each new device does a better job of MAINTAINING the integrity of my Entourage database, when I sync the device to my computer.

Problem is, we've NOW reached a point (somewhere around 10,930 contacts, it appears) where *Entourage* is dropping files. It's losing contacts. I had a meeting on Monday and came home from it and added five new manager friends to the database. They all work with someone who was already in my database, so I took her card and duplicated it (for the company name, address, and main number) and then edited each card to include their names, direct lines, email addresses, birthdays, whatever else came up during our meeting for the NOTES section, etc.

Yesterday, I noticed that all new files were missing. AND a filmmaker's file I had *updated* in the past 24 hours was now missing. So I did a little spot check of recently updated and/or created files and they were ALL gone. Entourage has gotten "full" from what I can tell. [9/8/09 NOTE! It has since been established that nothing was "full," but that my Microsoft Entourage database was corrupted and unstable. We performed a series of rebuilds and stopped subsequent data loss from occurring and have been mostly stable since May of 2009 on this issue.] I'm nervous to create new files if they're just going to go away. I'm even MORE nervous about the erosion of existing files I may not be actively using, as I'd not notice they're gone 'til LONG after I'd done a sync to my iPhone, thereby losing the "old" version altogether.

(Yes, we've done the whole Entourage support site, listserv, power-users Q&A thing at this point. Nada.)

Without going into the details of the glitches any deeper, I'll get to the point of this email.

It's become clear that my consumer-level database for contacts management (Entourage) is no longer sufficient. Since my contacts will only continue to grow, this isn't something I want to patch. I want to know what PROFESSIONAL-LEVEL software is in use out there for contacts management that will allow an import from Entourage (Note: If I import from iPhone, the categories and mail history from the past decade will be LOST and NOTES will be truncated. That is unacceptable.); that will allow for regular syncing between Entourage (which I will continue to use for mail from my computer) and iPhone (which I will continue to use for mail from my hand); and that WON'T lose, duplicate, mis-label, or otherwise hiccup (within reason, of course. I know that no software is perfect) my data when I sync.

NO, "Address Book" and "Mail" that are native to Mac will not work. "Thunderbird" has already been dismissed as an option. I do not want to maintain a separate Excel or Access or File Maker Pro database of contacts that cannot be ACTIVELY synced with incoming mail both at my iPhone and on my Mac. In case you've read this far and don't already know, "Entourage" is the Mac version of "Outlook." And no, I will not be switching to a PC. Ever. Nothing personal. I can take a PC apart and put it back together again blindfolded. I have great fondness for those machines. I prefer a Mac. Thank you. :)

Okay... so...

Any suggestions?

Yes, I could Google. But Google is going to tell me what designers want me to know about their product. I'm looking to hear from people who USE the products out there and who have the same number of contacts that I do (and roughly the same criteria for success of data management that I do) so that before I plunk down a few hundy, I know I'm getting something that's going to rock my world. :) Basically, I'm a consumer who has become a small business. Growing pains. I need to move up but am not sure to what.

Please pass along to your awesome geeky friends. :) I appreciate any ideas you might like to share.

Keep rockin', Hollywood Happy Hour!



September 8, 2009:

Just popping in to say that the decision this weekend to go to Mail, Address Book, and iCal came from Snow Leopard seeming to kill off more of Entourage's ability to play nice on my 'puter. So, since I was going to open my mind to ANY other software (after having been so married to Entourage, back in my post from May), I asked a friend who sweetly suggested I leave Entourage for "anything else" what he might recommend. My post to him:


September 4, 5:52pm:

Greg, what would you suggest I use instead? I'm all ears. I've surveyed MANY tech gurus (revealing to them exactly the extent of my needs: 11K+ contacts, over ten years of stored appointments--each meticulously linked to contacts, notes, project files, related information, categories) and no one can come up with data management (for contacts and appointments) as powerful as Entourage.

I would LOVE to use something else. But EVERYTHING else that has been suggested to me isn't for "power users." It's for people with like a few hundred (up to 3000) contacts and no need to have files linked back to one another within and across categories like I have them.

It's a key to my efficiency that this data works this way (even with the holes in the database, since I push it beyond the way Microsoft intended for a consumer-level user), so I'd be totally open to hearing other options. Just haven't heard any that come close to giving me what I need.


September 8, 2009:

Me again. At this point, a friend suggested some law firm software that links cases to witness lists and other handy categories and cross-purposing that seems interesting. Of course, I have to call the software provider (Abacus) for a quote, and I'm not feeling like that much of a small business, here. I'm feeling like a PERSON who just happens to be running a small business. But I'm getting it. I'm going to have to spend some money here. And for the right solution, I will. But first, to get my data stable. :)

Here's the chronology on that. This is long. Thank you in advance for reading. :)


August 31st: Installed Snow Leopard. Knew the Entourage database was unstable (see above), but felt the upgrade was safe, after repairing/backing up the database.

September 1st 7:15pm: Noticed Entourage messages were no longer searchable by keyword.

September 1st 11:45pm: Did Entourage database rebuild/replace, permissions repair, reset sync services. Now able to search Entourage messages via keyword.

September 4th 3pm: Entourage and Word stopped working. Spinning pinwheel of death upon every click within either program.

September 4th 5:27pm: Full reinstall of Microsoft Office seems to have fixed the problem. Successfully using Word and Entourage. Print to PDF in Word still occasionally causes a crash.

September 4th 11:35pm: Sync of Entourage calendar to iPhone calendar. Successful after three attempts (resetting sync history was the key). No sync of Entourage contacts to iPhone's Address Book (as I only do this once every two weeks or so, because it's hugely time consuming). Note: I *always* have Entourage overwrite iPhone, on these syncs, because syncing without overwriting yields duplicates and data loss, historically. Notice for the first time something called Mingler, eating up 99.9% of the CPU in Activity Monitor.

September 5th 10:43pm: I have 8142 duplicate entries in my contact file in Entourage. I kill them off.

September 5th 11:11pm: I have 3713 duplicate entries in my contact file in Entourage and Microsoft Sync Services crashes and reports. I attempt to sync my calendar on iPhone. No luck. I don't push it. Obviously, something's getting wonky.

September 6th: Contacts in Entourage (11,212 contacts when healthy) began reproducing themselves regularly. I killed off the dupes as they populated. Took screen captures along the way (I have 18 screen caps from between 11:01am and 7:10pm). Mingler seemed to be the big hog in the Activity Monitor, a process we've not seen until installing Snow Leopard. Also had reports of Microsoft Sync Services and Address Book Sync using 97% and 95% of the CPU, respectively. At one point (3:33pm), two Microsoft Sync Services were functioning at once, each using 77% of the CPU. Choosing to *wait* to delete dupes seemed to have no impact on whether more would be created. Each few moments, after Microsoft Sync Services would crash/report, there'd be a new round of dupes counting up in the bottom left corner of my Entourage contacts pane. This was all day September 6th. Screen captures taken throughout the day. Another eight screen caps taken after midnight on 9/7, 'til 1:53am. Greatest number of dupes at 12:18am (21,155 additional contacts).

September 7th 12:31am: Attempted to send an email to someone who has been in my address book at Entourage for years. He's missing. Uh-oh. Data loss. That's the one thing that's unacceptable. I can deal with duplication of data. Data loss? No.

September 7th 12:35am: Decided Entourage just wouldn't survive in Snow Leopard and committed to making the move to Address Book, iCal, and Mail (NOT ideal, for my needs--believe me, this is NOT what I want to use, at all. The linked contacts, the categories, the rules, the decade-plus of meticulously organized information in Entourage is NOT something I'm happy to lose, in exchange for a lovely "LUMP" of contact information not color coded, not categorized, not labeled as robustly as Entourage allowed, not linked to all prior communication and projects, etc. NOT happy. But it seems a necessary evil at this point) in order to avoid data loss and further database duplication. Hoping a native software set would be more stable for the data. Contact duplications got up to over 58,000 in Entourage. Attempted sync Entourage calendar to iPhone. Unsuccessful. Decided to not attempt an iPhone sync of *any* kind until things are more stable with the contacts. Created a PDF of contacts changed in the past 30 days at Entourage, as those would be the only ones in need of updating, should I have to revert to the last-synced iPhone version of the Entourage contacts file (11,212 contacts).

September 7th: Eleven hours of migration from Entourage to Address Book, iCal, and Mail. (2:27pm, closed Entourage hopefully for the last time. Settings: NO sync, Work Offline, in case need to relaunch.) Bringing over, one at a time, custom mailboxes, mail rules, signatures. Resetting appointments in iCal, changing alarms, To Do items, notes. Asked Address Book to merge duplicate contact files, as it reported finding 30,000 of them. Merge of data (repeated this process several times, until Address Book got down to 11,900 or so contacts, which was "close enough" for me to clean up by hand) caused many of the contact files to reproduce data from WITHIN themselves. Example: NOTES section of a contact was repeated over 100 times in more than a few contacts that were not duplicated in whole. Spot check revealed many instances of relabeled data in Address Book (all correct labels in Entourage were reset in Address Book, even though we've been syncing to iPhone by way of Address Book since November 2007 with no problem). Contacts I had "killed off" in Entourage still existed in Address Book (like, people who have passed away). Still, this clean-up didn't seem too overwhelming, so I began deleting duplicate entries and cleaning up duplicated NOTES fields within individual contacts. Trying to embrace this new software I'm not happy about using, because anything is better than data loss.

September 7th 11pm through 1:30am September 8th: processes started stalling out. Activity Monitor showed all three--Address Book, iCal, and Mail--not responding. I did a force-quit of each. Rebooted my machine. Upon restart and relaunch of Address Book, I was appalled to discover over 62,000 contacts, many with that reproduced content in their NOTES field. Awesome. Time for bed. There is no way I understand this. We're not syncing anything. Syncing is turned off at Microsoft Entourage and Microsoft Sync Services shouldn't even launch anymore. Ever. I've not attempted a sync with my iPhone--and will not, 'til we're stable--while this is happening and that means a piece of software that is not syncing over AIR or MobileMe (I don't have a MobileMe account; I sync through iTunes) is simply reproducing its contents... for fun?

September 8th 8am: Address Book stable at 62,617 contacts. I had gotten it down to 11,500 or so before 11pm on 9/7.


September 9th: We will go to the Genius Bar. Still not happy to have spent all of this time migrating only to have the data issues persist in native software. Definitely, I need something more powerful and robust for managing my information, but first I need it all to settle down and stabilize so I can get it moved over to wherever this new place is. Any suggestions--it's like I'm right back in May, asking this question again--for amazing contacts and appointments management and email, I'd love to hear it! Thanks. :)

Black MacBook 13.5" Intel Core-2 Duo, 4GB RAM, OS 10.6, iPhone 3G 16GB

Posted by bonnie at September 8, 2009 11:54 AM


I have not upgraded to SL however I'm getting the repeating a contact in my entourage. one contact and one phone number 1,200 a day. Did you ever find a fix? Running Entourage 12.2.0 Frighten to sync my I phone. BTW Take a look at Daylight by market circle works for mac and might be able to do what you need.
Mac Book Pro

Posted by: Eric at September 29, 2009 10:49 AM

Hi Eric,

I outline the steps I took to stop the reproductions in post number 10 here: http://forums.macosxhints.com/showthread.php?t=105156

Lemmeknow if that helps you. I definitely didn't sync ANYTHING until that ridiculous replication stopped. Wanted at least ONE place where my data was stable, even if not 100% up-to-date. :)

Thanks for the tip on Daylight. I've heard that one from others too. Gonna check that out. Thank you! :) And good luck to you. Not sure my fix will work with you, as they're saying mine was directly related to the Snow Leopard upgrade, but it was what the Genius Bar guy advised and it DID stop the bleeding. :)


Posted by: bon Author Profile Page at September 29, 2009 12:13 PM

I have just switched over to using Entourage ( was very leery because of it being a MS product)to manage my "Projects" and trying to do the whole GTD thing. It's been about 3 days now and I am noticing my tasks that were cross synced to different projects are either self-deleting or totally changing the criteria all together. I would love to hear of something that can be as powerful as Entourage seems to be on the surface. But I too need something more stable.



Posted by: Scott at October 7, 2009 2:49 PM

Hello from Russia!
Can I quote a post in your blog with the link to you?

Posted by: Polprav at October 16, 2009 7:04 AM

Jut curious to know where you landed with respect to your contacts management on this ... did you switch to DayLight?

Posted by: Oliver Keeton at April 7, 2010 2:24 PM

I didn't, Oliver. I'm still with Address Book (not 100% pleased) and iCal (almost 100% pleased). I've stopped the bleeding on data loss and dupes, which was the big issue. I've lost the robust labeling and categorizing, which makes me somewhat less efficient but I'm saving time now by not worrying about categorizing and labeling everything, so maybe there's a gift in there somewhere.

Basically, I'm still shopping. But I think it's going to take moving over to a more powerful (read: expensive) solution for small businesses and I'm not quite ready to do that just yet. I'm also doing more of my data management on my internal server's wiki.

Posted by: bon Author Profile Page at April 7, 2010 9:31 PM

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