D5 to D6 Update path

how are they not being updates properly? Do you have an example table you can dump for testing... content_node_field and content_node_instance before and after update?

The following changes are not made (still needed):

content_node_field_instance:
widget_type: "image" --> "imagefield_widget"
widget_module: "" --> "imagefield"
widget_active: "0" --> "1"

content_node_field
db_columns: shouldn't be empty?

Here are the two tables before and after for a (fortunately) very simple site I've just upgraded from Drupal 5.9/Imagefield 5.x-2.1 to Drupal 6.4/Imagefield 6.x-3.0-alpha1.

Here's a workaround that kinda works. Sorry I can't provide a patch, but I'm not at all familiar with how .install files work, and that's where the problem is bound to be.

1. Make a new field, either using the same site/database with a different field name, or a different site/database, which works the way you want your old field to work.
2. In the `content_node_field` table, copy the content of the `db_columns` field from your new (imagefield) field to your old (imagefield) field. (okay, the two contexts for the word 'field' is confusing here). In my case this content was 'a:3:{s:3:"fid";a:2:{s:4:"type";s:3:"int";s:8:"not null";b:0;}s:4:"list";a:3:{s:4:"type";s:3:"int";s:4:"size";s:4:"tiny";s:8:"not null";b:0;}s:4:"data";a:2:{s:4:"type";s:4:"text";s:9:"serialize";b:1;}}', but I expect this will vary depending on how you've configured your field.
3. In the `content_node_field_instance` field for your old (imagefield) field, change `widget_type` to 'imagefield_widget', `widget_module` to 'imagefield', and `widget_active` to '1'
4. You will probably need to clear your Drupal cache (using Devel module or whatever), and check your field's config and display settings at '/admin/content/node-type/*'.

I'm finding that on old nodes, image thumbnails are not being displayed on the edit form, but this may be an unrelated issue, and I can live with that. New uploaded images are fine.

I had this issue too. Matthew's post #5 did work, although it took a few tries to get right (once, the database column content_type_TYPENAME.field_FIELDNAME_fid got dropped from the database).