How can I sync my Outlook calendars?

Episode 999

John from St. Georges, UT

John can't get his Outlook calendar to sync. Leo says syncing is a dark art. Issues in sync include data duplication, and multiple calendar users. His issue is with Outlook and Google Calendar.

Leo says that Outlook is a poorly written Calendar. Leo advises getting rid of it altogether and relying solely on Google Calendar. It'll work with anything, any platform (except Outlook, obviously), and it'll sync. He should make sure Outlook email and announcements are set in his settings. He should have no issues once he goes to Google exclusively.

How can I sync my iPhone without having to upgrade my entire operating system?

Episode 975

Scott from Yucaipa, CA

Scott just got a new iPhone 5 and found out he can't use it without iTunes 11 -- he would have to update his OS as well! Leo says that's true, but Apple handles sync over the air now, so he doesn't really have to sync directly. He can use iCloud and iTunes Match, if he's a subscriber of it, to sync his music. He can also sync via Google Services.

How can I sync files from a school network to my home?

Episode 970

Perry from Scio, OR

Perry is a teacher, and he needs to sync files back from the school's server to his office computer so he can then sync them through DropBox. Leo suggests a utility called Second Copy. The chatroom likes SyncBack. Microsoft has SyncToy, but the latest version has some issues. Nice thing about Syncback and SecondCopy is that they do WildCards.

Another option is SpiderOak, but it's a paid service.

Why is Sugar Sync adding more to my database file names every time it syncs?

Episode 918

Eric from Gathersberg, MD

Eric is using Sugar Sync with Microsoft Access, and every time it uploads his files to sync it, it gives them a longer and longer file name. Leo says it's doing this because Sugar Sync doesn't know which copy is the most recent and the one he wants, so it saves them all. It has to increase the file name of each one because there are naming conflicts otherwise.

Why is iCal syncing to my wife's profile instead of mine?

Episode 907

Chris from Valencia, CA

Since Chris says he can sync his contacts just fine, Leo says to check the settings to see if iCal is syncing to something else, like Google Calendar. It won't sync on it's own, so there has to be a setting in there that's been changed. It can get very confusing when using multiple Apple ID's, and it's possible that he got the wires crossed somewhere. At this point it may be a good idea to delete both accounts and start over.