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<div class="" style="word-wrap:break-word">After much messing about, I finally realized I'd gotten to the point where I could write a simple script to attempt to generate the problem and did so. I'be now reproduced the problem on x86 Linux with v2.86 tag in
 the git repo, which made things much easier. 
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<div class="">The attached tar ball contains the script, my config file, my Makefile. The directories success and failure contain a capture of a v2.86 failure and success. The DNSSEC reply causing the failure is interesting.</div>
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<div class=""><span class="" style="font-style:normal"><font face="Menlo" class="">failure: 19<span class="x_Apple-tab-span" style="white-space:pre">
</span>0.098203<span class="x_Apple-tab-span" style="white-space:pre"> </span>8.8.4.4<span class="x_Apple-tab-span" style="white-space:pre">
</span>0.0.0.0<span class="x_Apple-tab-span" style="white-space:pre"> </span>DNS<span class="x_Apple-tab-span" style="white-space:pre">
</span>319<span class="x_Apple-tab-span" style="white-space:pre"> </span>Standard query response 0x2b96 DS
<a href="http://admanmedia.com" class="">admanmedia.com</a> CNAME <a href="http://admanmedia.com.edgekey.net" class="">
admanmedia.com.edgekey.net</a> RRSIG CNAME <a href="http://e11261.dscd.akamaiedge.net" class="">
e11261.dscd.akamaiedge.net</a> SOA <a href="http://n0dscd.akamaiedge.net" class="">
n0dscd.akamaiedge.net</a> OPT</font></span></div>
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<div class=""><span class="" style="font-style:normal"><font face="Menlo" class="">success: 19<span class="x_Apple-tab-span" style="white-space:pre">
</span>7.418939<span class="x_Apple-tab-span" style="white-space:pre"> </span>8.8.4.4<span class="x_Apple-tab-span" style="white-space:pre">
</span>0.0.0.0<span class="x_Apple-tab-span" style="white-space:pre"> </span>DNS<span class="x_Apple-tab-span" style="white-space:pre">
</span>888<span class="x_Apple-tab-span" style="white-space:pre"> </span>Standard query response 0xff70 DS
<a href="http://admanmedia.com" class="">admanmedia.com</a> NSEC3 RRSIG SOA <a href="http://a.gtld-servers.net" class="">
a.gtld-servers.net</a> RRSIG NSEC3 RRSIG OPT</font></span></div>
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<div class="">The directory new contains a capture of sequence that caused the failure against <span class="" style="font-size:13px">2.87test5-16-g27ce754 </span>and dnsmasq abandoned the validation and did not loop. Certainly better than what it used to do,
 but is it correct?</div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: dumping UDP packet 15 mask 0x0001</span></div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: query[A]
<a href="http://cs.admanmedia.com" class="">cs.admanmedia.com</a> from 127.0.0.1</span></div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: dumping UDP packet 16 mask 0x0004</span></div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: forwarded
<a href="http://cs.admanmedia.com" class="">cs.admanmedia.com</a> to 8.8.4.4</span></div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: dumping UDP packet 17 mask 0x0008</span></div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: dumping UDP packet 18 mask 0x0010</span></div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: dnssec-query[DS]
<a href="http://admanmedia.com" class="">admanmedia.com</a> to 8.8.4.4</span></div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: dumping UDP packet 19 mask 0x0020</span></div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: detected DNSSEC dependency loop involving
<a href="http://admanmedia.com" class="">admanmedia.com</a></span></div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: validation
<a href="http://cs.admanmedia.com" class="">cs.admanmedia.com</a> is ABANDONED</span></div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: reply
<a href="http://cs.admanmedia.com" class="">cs.admanmedia.com</a> is 88.214.206.247</span></div>
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<span class="" style="font-variant-ligatures:no-common-ligatures">Jan 17 13:53:17 dnsmasq[143548]: dumping UDP packet 20 mask 0x0002</span></div>
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