The Macbook and the Blackberry


Macbook plus Blackberry equals disaster

Slick Apple marketing campaigns would have you believe that Apple Mac computers are the panacea of the computing world.  What the Mac Guy states above are his exact words.

  • Panacea: (n) ((Greek mythology) the goddess of healing; daughter of Aesculapius and sister of Hygeia)
  • Panacea: (n) panacea, nostrum, catholicon, cure-all (hypothetical remedy for all ills or diseases; once sought by the alchemists)
I'm here to report that while Macs are largely immune from Viruses, Trojans, and Spyware they have their own set of problems.

March 14, 2009 Mission:  Setup a Blackberry 8830 to Sync with Entourage on a black Macbook laptop. The customer was converting from a Palm based phone, because it was having difficulties syncing with Macbook.  This customer is with Sprint, and Sprint does not offer the iPhone. We disabled the Palm startup applications, in Leopard's User account settings, to prevent interference between the Palm and the Blackberry. A cursory inspection of her Entourage 2008 revealed about 1,700 contacts, and about 2,400 Calendar events, spanning back to 1999. There were numerous entries, doubled, tripled, quadrupled, quintupled, octupled yes even some were duplicated 10 times in a single day, mainly in the year 2007, which, according to the customer, was the result of purchasing the Palm Phone.   Evidently the hotsync operation caused this.

Apple's operating system has a function called Sync Services.  It provides the synchronization service between the devices - in our case the phone, and Apple's built-in iCal and the Address Book.   iCal and Address Book are included with OS X (pronounced OS "10") and compared to Windows XP, there is no other free equivalent program which is included by Microsoft.  iCal lets you enter in Calendar events, very similar to Outlook's Calendar, but again, you don't have to pay Microsoft to get this feature.   In addition it can sync to it's on line Service "MobileMe."  This may also be named ".Mac", especially by Microsoft Software.  The customer was signed up for MobileMe, but does not use MobileMe, and for the sake of Tech Savvy Mac people who may be reading this, when we reset the Sync relationship, we elected to overwrite all prior MobileMe entries.

Following this paragraph, I will reference the "Crackberry Forum Posting," located here, which gave us the most operational success (up til 10pm March 14, 2009), and the problem was about 80% solved (more on this later). Also, prior to my visit, the customer had spent about a week troubleshooting this problem on her own, with email support from the software creators of "The Missing Sync," by a software company called  Therefore the focus of the following paragraphs is with Blackberry's own PocketMac.  We disabled the startup services for the MarkSpace software.  All syncing was done through the USB port, not through Bluetooth - evidently this functionality does not work.

How Sync Services syncs with a device:  To sync contacts and calendar from Entourage, it's really a double hop.  You setup Entourage to sync with iCal and the Address Book, then Sync Services syncs iCal and the Address Book with the Device, through special Blackberry software (PocketMac or Missing Link) - which I'll get into this later.  Therefore, iCal and Address book must be in good working order and problems in Entourage Calendars and Address Book (like the double, triple, and quadruple calendar entries from above) will propogate to iCal and Address Book respectively.  Also, we performed full exports of iCal, Address Book, and Entourage Contacts and Calendar (into their own individual RGE files before starting to do anything.  Also, according to the Crackberry recommendations - disabling all sync relationships in Entourage

Problem #1:  Getting rid of old appointments.  Clearly there was no benefit to keeping appointments back to 1998, so we decided we wanted everything up to the last three years.  In iCal go to Preferences, Advanced Settings, you will find a checkbox that states "Delete events 30 days after they have passed." We checked it.  iCal warned us of what we were about to do.  We clicked ok.  We waited.  Nothing.  Nothing happened.  Nothing older than 30 days was deleted.  According to this Apple Forum Discussion, this function is broken in iCal in Leopard.   So off we went, taking the Discussion recommendation - typing in the Search window common letters - 'a', then 'e', then 'i', and manually deleting old appointments from the listview "find results" window. Our Core Duo 2 2.0 Ghz MacBook with 2 gigs ram had slowed considerably during this operation, as it struggled to delete such a large amount of appointments.  While there are more draconian ways of deleting iCal information - such as stopping certain services and deleting iCal's data folders, within 30 minutes we had everything we wanted deleted.  In retrospect, deleting the entire iCal data contents would have been easier in the long run, because we would have to do the same thing in Entourage - clean up, and we were going to resync Entourage Calendar with iCal anyway, and the results would have been clean anyway.  Going by the Crackberry article (link 3 paragraphs above), we exported the smaller calendar set (a second time), and reimported.  This resets the sync relationship. We did the same with the address book.  In this instance the customer cleaned out all contact entries herself in Address Book and the address book was empty.  Nevertheless we exported and re-imported.

Problem #2:  Entourage Calendar Cleanup.  We eliminated just over 700 duplicated Calendar entries by hand.  Later on we learned of a Jolly Roger Script would could have streamlined this process considerably, but by the time we discovered it we had everything set the way we wanted. This took about an hour.  Jolly Roger's Calendar Duplicates eliminator is here:

Epilogue: Following the Crackberry article, we did the restarts of the Mac at the prescribed intervals, installed the PocketMac software plus the USB Patch, available from followed by restarting the computer.  We did not uninstall MarkSpace, and perhaps we should have. Our first Sync was entirely successful, we setup PocketMac to sync (counter-intuitively) with iCal and Address Book (we did not select Entourage Calendar or Contacts), and for Calendar we wanted only the last year - 365 days worth of appointments, not the last five years (we eliminated every Calendar event before 2004 in Entourage). In Address Book, we got all but 70 contacts, which seemed odd.   In calendar, we think we got all the calendar events.

Problem #3: Subsequent Syncs.  The first sync went completely through - we had 39 calendar conflicts, which we corrected, but after that, even if we didn't change information, sync's would take nearly an hour and get stuck on the status "synchronizing data."  This was after it went through Contacts and Calendar.  We were not syncing anything else in PocketMac - no Music, Email, Notes, or Tasks, so this became our problem #3.

There are so many suggested workarounds which may or may not resolve this issue, and as it was getting late into the evening, we'll have to address this with the customer in the morning. There are numerous google links on the subject, many of which have differing and conflicting information.  Some solutions:

  • Wipe the blackberry handheld, resend the Service books from Sprint, and try resyncing again. This has worked for some users.
  • Some users state to stop using PocketMac and use Missing Sync
  • Some users state to stop using Missing Sync and use Pocket Mac
  • Some users state use DataPurgeUI and SyncClean to clean up the BB
  • Some users state using the above two utilities makes it sync successfully one time but subsequent syncs don't work.
  • Some dual boot into Windows XP and sync on the Windows platform - Blackberry Desktop Manager and Outlook

As I learn new information, I will add to this page.  If you have comments email them to me and I will post them.  I don't want to start a PC vs. Mac flaming war, I want to resolve a problem. As it stands now, the customer has the phone, as it turns out, on a 30 day trial.  For the moment, she has her eye on an iPhone from ATT.