When you apply a stroke to type, it can only be external. By default, when you apply a stroke to a box, InDesign will center your stroke instead of having it external like you have it for your type. So it looks like your stroke is disappeared but in actual fact is there.
Here is how you handle it:
- Once you have converted your type to outlines go to your Stroke Palette. If it isn't open then go to Window > Stroke. Now you have your palette with all of its options.
- About half way down the palette you will see an entry that says Align Stroke and three sqaures. The first one will center your stroke, the second one will create an internal stroke and the third one an external stroke. If you click on the last one, your stroke will reappear and will look like when your outlines were originally type.