You have to change the size of the image frame up to the bleed with the selection tool. It will never happen automatically with any command. Then you will have to scale the image to fill the frame up to the bleed.
Also check that you are not in preview mode. Hit the W key.
Can't be Preview mode if the guides are showing, but that is an important point.
...but when I drag to extend the image to fit the bleed, the image does not show up between the edge of the page and the bleed area.
It sounds to me like you are only dragging the frame to the bleed guides, leaving the image itself unaffected. Press/hold Ctrl/Cmd before you click the frame handle, then drag, and the image will respond together with the frame.
In your screenshot you show the page size as 11.125 inches x 5.375 inches.
Are you sure this is the final trim size of the sheet? 11 x 5.25 would seem to be more logical.
In the Document Setup the page size should be the same as the final trim size.
All bleeds are added only in the Bleed fields
In the screenshot the image frame is only moved to the page size. (the Black border)
Anything that needs to bleed must be enlarged to the size of the bleed border (the Red border)
The magenta border is only the margins inside the page
Thank you! Yes, that's what was happening. I'm unclear on what it means to expand the frame without expanding the image inside, but holding ctrl while dragging the corners worked.
... but don't forget to add shift to the cmd when dragging that image - so you keep the proportions.