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Here is a blog post about it

Post a UIImage to the web | Iphone Noob

Here is the meat of the code to post

NSData *imageData = UIImageJPEGRepresentation(image.image, 90);
	// setting up the URL to post to
	NSString *urlString = @"http://iphone.zcentric.com/test-upload.php";
	
	// setting up the request object now
	NSMutableURLRequest *request = [[[NSMutableURLRequest alloc] init] autorelease];
	[request setURL:[NSURL URLWithString:urlString]];
	[request setHTTPMethod:@"POST"];
	
	/*
	 add some header info now
	 we always need a boundary when we post a file
	 also we need to set the content type
	 
	 You might want to generate a random boundary.. this is just the same 
	 as my output from wireshark on a valid html post
	*/
	NSString *boundary = [NSString stringWithString:@"---------------------------14737809831466499882746641449"];
	NSString *contentType = [NSString stringWithFormat:@"multipart/form-data; boundary=%@",boundary];
	[request addValue:contentType forHTTPHeaderField: @"Content-Type"];
	
	/*
	 now lets create the body of the post
	*/
	NSMutableData *body = [NSMutableData data];
	[body appendData:[[NSString stringWithFormat:@"\r\n--%@\r\n",boundary] dataUsingEncoding:NSUTF8StringEncoding]];	
	[body appendData:[[NSString stringWithString:@"Content-Disposition: form-data; name=\"userfile\"; filename=\"ipodfile.jpg\"\r\n"] dataUsingEncoding:NSUTF8StringEncoding]];
	[body appendData:[[NSString stringWithString:@"Content-Type: application/octet-stream\r\n\r\n"] dataUsingEncoding:NSUTF8StringEncoding]];
	[body appendData:[NSData dataWithData:imageData]];
	[body appendData:[[NSString stringWithFormat:@"\r\n--%@--\r\n",boundary] dataUsingEncoding:NSUTF8StringEncoding]];
	// setting the body of the post to the reqeust
	[request setHTTPBody:body];
	
	// now lets make the connection to the web
	NSData *returnData = [NSURLConnection sendSynchronousRequest:request returningResponse:nil error:nil];
	NSString *returnString = [[NSString alloc] initWithData:returnData encoding:NSUTF8StringEncoding];