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Content-length

Entity-header field indicates the size of the entity-body.

Content-type

The Content-Type entity-header field indicates the media type of the entity-body sent to the recipient or, in the case of the HEAD method, the media type that would have been sent had the request been a GET.



Others

Example

Charset utf-8 host graph.microsoft.com content-length 111 expect 100-continue connection keep-alive odata.type microsoft.graph.opentypeextension extensionname com.test.nickname date openextension;content-type was not specified and it was going as text

from question  

Getting code=OrganizationFromTenantGuidNotFound while updating group using Microsoft Graph

The most common quirks with ie9 that often do not bother web browsers are mismatches in content-length well this did bother safari last time i looked possibly content-type this acts in reverse - ie9 sometimes correctly gleans html mimetype even if the content-type is wrong connection close;so yes it could be a problem with http pipelining specifically if you pipeline a request with invalid content-length and not even chunked-transfer-encoding ie might wait for the request to finish

from question  

IE9 and Python issues?

...web api relies on system.net.http library for getting request headers and system.net.http library gives a null for httprequestmessage s content.headers.contenttype in this case and web api sees that content-length is greater than 0 but no content-type header and hence returns a 415 unsupported media type

from question  

Web API unsupported media type when uploading - charset not passed

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