Sharing broadband with my old imac

Hi I have an emac running tiger and a very old imac, the first model, currently running 8.6. I bought a wireless ethernet bridge to share broadband and configured everything with the internet setup assistant. This ran beautifully for a day, with IE browsing the web and outlook picking up mail.
Now it has stopped. Both applications just give a failed to connect error. I have looked in the tcp ip and ethernet control panels and everything seems to be ok. The wireless network is working, I can ping both the ethernet bridge and the imac from my emac.
2 questions
1) What can I do to diagnose and fix the error?
2) Would any of this be significantly easier under Mac OS 9?
Oh yes and,
3) Can I get filesharing working in either direction, now my network is up

As Simon says, Tiger and 8.6 won't network. Either you upgrade to OS 9 (it has TCP\IP networking as a FileSharing option) or downgrade to Panther—which has very balky networking compared to 8 and 9 BTW; Jaguar was apparently slicker—or you'll have to be content w/ emailing or sneakerware between machines. Given Apple's no-recordable-media stinginess on the original iMac, that latter is only an option if you have an outboard device for it.
The procedure's similar once you have two compatible OS's, though the names of the controls for the settings are unaccountably different. Enable sharing c/w owner's names and passwords on each (SystemPrefs or Control Panels). Enable an ethernet connection on each (NetworkPane, AppleTalkCP). Select items to be shared on th old-world machine, and set their sharing status as desired (GetInfo…).
If you are doing anything more complex than the same—letter for letter mind you—owner/pwrd on both, go back to FileSharing CP and name your other users. On your X machine, if you want access to anything beyond Shared and Public folders by the admin, hire a sysadmin. Hire one anyway if you can afford it; Tiger may have simmered down, but to one used to the simple elegance of old AppleTalk networking, X's is a jungle of jargonry and nerdisms—check the Networking discussions for yourself.
Finally. w/ both machines plugged into a 'hot' ethernet connection—another active computer or a router—boot up and find your target (Chooser or the Network blob-thingy-that-isn't-an-application-or-CP-but-exists-only-as-a-poofter-in-the -Dock-and-Sidebar-soApple-calls-it-an-alias-though-you-never-see-it's-original) And if you like nerdery as much as X, you can also find and type in IP addies (Finder>Go>Connect to server…, Chooser: Enter IP address)
There's lots of stuff in earlier threads in this discussion and the X discussions as well as the Apple Knowledge base, and I seem to have bookmarks for none of them, sorry. But this one is a gem: Francine's posta are invariably heplful:
Networking 101 Time spent browsing there and in the Users' Tips library will be well-spent in any case. Googlig can also be helpful, but the best dollars you ever spend may be for David Pogue's Missing Manuals on yr two OS's. However, to finish as we started: Simon says Tiger and 8,6 won't get along. Believe him.

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