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I'm running WordPress on an IIS test server. mod_rewrite is enabled and I've modified my web.config to support permalinks. c:\windows\temp has been modified to allow Modify access to both IUSRS and IIS_IUSRS.

Although the permalinks themselves work, I'm having an issue with broken images. But only some broken images. Any image I've uploaded myself via the media manager is broken. Any image that WP generates (e.g. the featured image), is appearing.

I've checked that the images I've uploaded actually exist in the location stated (they do) but they are showing up broken. When I try to pull the images up in the browser, I get that 500.5 error.

What am I missing?

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I figured it out! I didn't have Modify permissions set for IIS_IUSRS on the /wp_content/uploads folder.

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    You should mark this answered ;-) – jgraup Dec 18 '15 at 17:24
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    Please expand this answer by explaining how to make that change. – s_ha_dum Dec 18 '15 at 17:46

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