Symptoms
Considering the following scenario:
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User A and user B are using the Microsoft Skype for Business on Mac client.
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User A sends an instant message (IM), for example, "test1" to user B, and user B does not respond.
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After several minutes, user A sends another message, for example, "test2" to user B, and user B still does not respond.
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User A sees a conversation with user B under the Chats tab in the Skype for Business on Mac client. The conversation shows messages "test1"Â and "test2."
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User A deletes the conversation with user B.
 
After some time, the conversation with user B appears again in the Chats tab with only the message "test1." It's expected that all messages in the conversation with user B will be deleted.
Resolution
To fix this issue, install the following updates:
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The July 2018 cumulative update 6.0.9319.534 for Skype for Business Server 2015, Web Components Server.
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The July 2018 cumulative update 6.0.9319.534 for Skype for Business Server 2015, Front End Server and Edge Server.