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        <base href="https://hibernate.atlassian.net"> 
        <title>Message Title</title> 
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    <body class="jira" style="color: #333333; font-family: Arial, sans-serif; font-size: 14px; line-height: 1.429"> 
        <table id="background-table" cellpadding="0" cellspacing="0" width="100%" style="border-collapse: collapse; mso-table-lspace: 0; mso-table-rspace: 0; background-color: #f5f5f5; border-collapse: collapse; mso-table-lspace: 0; mso-table-rspace: 0" bgcolor="#f5f5f5"> <!-- header here --> 
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                                    <td id="header-avatar-image-container" valign="top" style="padding: 0; border-collapse: collapse; vertical-align: top; width: 32px; padding-right: 8px" width="32"> <img id="header-avatar-image" class="image_fix" src="https://secure.gravatar.com/avatar/3a208a9ac288f48a64a5f002ef55a4eb?d=https%3A%2F%2Favatar-management--avatars.us-west-2.prod.public.atl-paas.net%2Finitials%2FAH-6.png" height="32" width="32" border="0" style="border-radius: 3px; vertical-align: top"> </td> 
                                    <td id="header-text-container" valign="middle" style="padding: 0; border-collapse: collapse; vertical-align: middle; font-family: Arial, sans-serif; font-size: 14px; line-height: 20px; mso-line-height-rule: exactly; mso-text-raise: 1px"> <a class="user-hover" rel="xxlali" style="color:#6c797f;; color: #3b73af; text-decoration: none" id="email_xxlali" href="https://hibernate.atlassian.net/secure/ViewProfile.jspa?accountId=557058%3Add96fccc-1289-4d99-810b-5723cdd171e2"> Ali Hopyar </a> <strong>updated</strong> an issue </td> 
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                    <td id="email-content-container" style="padding: 0; border-collapse: collapse; padding: 0 20px"> 
                        <table id="email-content-table" cellspacing="0" cellpadding="0" border="0" width="100%" style="border-collapse: collapse; mso-table-lspace: 0; mso-table-rspace: 0; border-spacing: 0; border-collapse: separate"> 
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                                <tr> <!-- there needs to be content in the cell for it to render in some clients --> 
                                    <td class="email-content-rounded-top mobile-expand" style="padding: 0; border-collapse: collapse; color: #ffffff; padding: 0 15px 0 16px; height: 15px; background-color: #ffffff; border-left: 1px solid #cccccc; border-top: 1px solid #cccccc; border-right: 1px solid #cccccc; border-bottom: 0; border-top-right-radius: 5px; border-top-left-radius: 5px; height: 10px; line-height: 10px; padding: 0 15px 0 16px; mso-line-height-rule: exactly" height="10" bgcolor="#ffffff">&nbsp;</td> 
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                                    <td class="email-content-main mobile-expand " style="padding: 0; border-collapse: collapse; border-left: 1px solid #cccccc; border-right: 1px solid #cccccc; border-top: 0; border-bottom: 0; padding: 0 15px 0 16px; background-color: #ffffff" bgcolor="#ffffff"> 
                                        <table class="page-title-pattern" cellspacing="0" cellpadding="0" border="0" width="100%" style="border-collapse: collapse; mso-table-lspace: 0; mso-table-rspace: 0"> 
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                                                    <td class="page-title-pattern-first-line " style="padding: 0; border-collapse: collapse; font-family: Arial, sans-serif; font-size: 14px; padding-top: 10px"> <a href="https://hibernate.atlassian.net/browse/HHH?atlOrigin=eyJpIjoiYmJmYzM1YjgzNmMxNGVjODg4ZmRjZmZkOWIzNTdmMmUiLCJwIjoiaiJ9" style="color: #3b73af; text-decoration: none">Hibernate ORM</a> / <a href="https://hibernate.atlassian.net/browse/HHH-14079?atlOrigin=eyJpIjoiYmJmYzM1YjgzNmMxNGVjODg4ZmRjZmZkOWIzNTdmMmUiLCJwIjoiaiJ9" style="color: #3b73af; text-decoration: none"><img src="cid:jira-generated-image-avatar-109663fa-b4a8-40f2-969d-718263cd404f" height="16" width="16" border="0" align="absmiddle" alt="Bug" style="vertical-align: text-bottom"></a> <a href="https://hibernate.atlassian.net/browse/HHH-14079?atlOrigin=eyJpIjoiYmJmYzM1YjgzNmMxNGVjODg4ZmRjZmZkOWIzNTdmMmUiLCJwIjoiaiJ9" style="color: #3b73af; text-decoration: none">HHH-14079</a> </td> 
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                                                    <td style="vertical-align: top;; padding: 0; border-collapse: collapse; padding-right: 5px; font-size: 20px; line-height: 30px; mso-line-height-rule: exactly" class="page-title-pattern-header-container"> <span class="page-title-pattern-header" style="font-family: Arial, sans-serif; padding: 0; font-size: 20px; line-height: 30px; mso-text-raise: 2px; mso-line-height-rule: exactly; vertical-align: middle"> <a href="https://hibernate.atlassian.net/browse/HHH-14079?atlOrigin=eyJpIjoiYmJmYzM1YjgzNmMxNGVjODg4ZmRjZmZkOWIzNTdmMmUiLCJwIjoiaiJ9" style="color: #3b73af; text-decoration: none">Orphan removal does not work on session.update function</a> </span> </td> 
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                                    <td class="email-content-main mobile-expand  wrapper-special-margin" style="padding: 0; border-collapse: collapse; border-left: 1px solid #cccccc; border-right: 1px solid #cccccc; border-top: 0; border-bottom: 0; padding: 0 15px 0 16px; background-color: #ffffff; padding-top: 10px; padding-bottom: 5px" bgcolor="#ffffff"> 
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                                                    <th style="color: #707070; font: normal 14px/20px Arial, sans-serif; text-align: left; vertical-align: top; padding: 2px 0">Change By:</th> 
                                                    <td style="padding: 0; border-collapse: collapse; font: normal 14px/20px Arial, sans-serif; padding: 2px 0 2px 5px; vertical-align: top"> <a class="user-hover" rel="xxlali" style="color:#6c797f;; color: #3b73af; text-decoration: none" id="email_xxlali" href="https://hibernate.atlassian.net/secure/ViewProfile.jspa?accountId=557058%3Add96fccc-1289-4d99-810b-5723cdd171e2"> Ali Hopyar </a> </td> 
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                                    <td class="email-content-main mobile-expand  issue-description-container" style="padding: 0; border-collapse: collapse; border-left: 1px solid #cccccc; border-right: 1px solid #cccccc; border-top: 0; border-bottom: 0; padding: 0 15px 0 16px; background-color: #ffffff; padding-top: 5px; padding-bottom: 10px" bgcolor="#ffffff"> 
                                        <table class="text-paragraph-pattern" cellspacing="0" cellpadding="0" border="0" width="100%" style="border-collapse: collapse; mso-table-lspace: 0; mso-table-rspace: 0; font-family: Arial, sans-serif; font-size: 14px; line-height: 20px; mso-line-height-rule: exactly; mso-text-raise: 2px"> 
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                                                    <td class="text-paragraph-pattern-container mobile-resize-text " style="padding: 0; border-collapse: collapse; padding: 0 0 10px"> <span class="diffcontext">Let's say I have two entites like <br><br>{code:java}@Table(name = "parent_entity")<br>@Entity(name = "ParentEntity")<br>public class ParentEntity extends PersistentEntity {<br> <br> @OneToOne(cascade = CascadeType.ALL)<br> @JoinColumn(name = "inner_entity")<br> private InnerEntity innerEntity = new InnerEntity();<br><br> public InnerEntity getInnerEntity() {<br>&nbsp;&nbsp;return innerEntity;<br> }<br><br> public void setInnerEntity(InnerEntity innerEntity) {<br>&nbsp;&nbsp;this.innerEntity = innerEntity;<br> }<br> <br>}<br><br>@Table(name = "inner_entity")<br>@Entity(name = "InnerEntity")<br>public class InnerEntity extends PersistentEntity {<br> <br> @OneToMany(mappedBy = "innerEntity", cascade = CascadeType.ALL, orphanRemoval = true)<br> private List&lt;ChildEntity&gt; children = new ArrayList&lt;&gt;();<br><br> public List&lt;ChildEntity&gt; getChildren() {<br>&nbsp;&nbsp;return children;<br> }<br><br> public void setChildren(List&lt;ChildEntity&gt; children) {<br>&nbsp;&nbsp;this.children = children;<br> }<br> <br>}<br><br>@Table(name = "child_entity")<br>@Entity(name = "ChildEntity")<br>public class ChildEntity extends PersistentEntity {<br> <br> @ManyToOne<br> @JoinColumn(name = "inner_entity")<br> private InnerEntity innerEntity;<br> <br> @Column(name = "child_value")<br> private String childValue;<br><br> public InnerEntity getInnerEntity() {<br>&nbsp;&nbsp;return innerEntity;<br> }<br><br> public void setInnerEntity(InnerEntity innerEntity) {<br>&nbsp;&nbsp;this.innerEntity = innerEntity;<br> }<br><br> public String getChildValue() {<br>&nbsp;&nbsp;return childValue;<br> }<br><br> public void setChildValue(String childValue) {<br>&nbsp;&nbsp;this.childValue = childValue;<br> }&nbsp;&nbsp;<br>}<br>{code}<br><br>When I call session.update with parent entity, orphanRemoval does not have any affect. It does not delete child entity and relationship between parent and child.<br><br><br><br>I have tried with 5.3.7.Final, 5.4.15.Final, 5.4.16.Final and 5.4.17 Final</span> <span class="diffaddedchars" style="background-color:#ddfade;"><br><br><br><br>Test Case can be found in attachment</span> </td> 
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                                    <td class="email-content-main mobile-expand " style="padding: 0; border-collapse: collapse; border-left: 1px solid #cccccc; border-right: 1px solid #cccccc; border-top: 0; border-bottom: 0; padding: 0 15px 0 16px; background-color: #ffffff" bgcolor="#ffffff"> <script type="application/ld+json">
{
  "@context": "http://schema.org",
  "@type": "EmailMessage",
  "description": "View Issue",
  "potentialAction": {
    "@type": "ViewAction",
        "target": "https://hibernate.atlassian.net/browse/HHH-14079?inbox=true&",
    "name": "View Issue"
      },
  "publisher": {
    "@type": "Organization",
    "name": "Atlassian",
    "url": "https://www.atlassian.com"
  }
}
</script> 
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                                                    <td id="actions-pattern-container" valign="middle" style="padding: 0; border-collapse: collapse; padding: 10px 0 10px 24px; vertical-align: middle; padding-left: 0"> 
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                                                                    <td class="actions-pattern-action-icon-container" style="padding: 0; border-collapse: collapse; font-family: Arial, sans-serif; font-size: 14px; line-height: 20px; mso-line-height-rule: exactly; mso-text-raise: 0; vertical-align: middle"> <a href="https://hibernate.atlassian.net/browse/HHH-14079#add-comment?atlOrigin=eyJpIjoiYmJmYzM1YjgzNmMxNGVjODg4ZmRjZmZkOWIzNTdmMmUiLCJwIjoiaiJ9" target="_blank" title="Add Comment" style="color: #3b73af; text-decoration: none"> <img class="actions-pattern-action-icon-image" src="cid:jira-generated-image-static-comment-icon-9f3f5264-eae3-45b8-a3c5-40677cbdad7f" alt="Add Comment" title="Add Comment" height="16" width="16" border="0" style="vertical-align: middle"> </a> </td> 
                                                                    <td class="actions-pattern-action-text-container" style="padding: 0; border-collapse: collapse; font-family: Arial, sans-serif; font-size: 14px; line-height: 20px; mso-line-height-rule: exactly; mso-text-raise: 4px; padding-left: 5px"> <a href="https://hibernate.atlassian.net/browse/HHH-14079#add-comment?atlOrigin=eyJpIjoiYmJmYzM1YjgzNmMxNGVjODg4ZmRjZmZkOWIzNTdmMmUiLCJwIjoiaiJ9" target="_blank" title="Add Comment" style="color: #3b73af; text-decoration: none">Add Comment</a> </td> 
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                                </tr> <!-- there needs to be content in the cell for it to render in some clients --> 
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                                    <td class="email-content-rounded-bottom mobile-expand" style="padding: 0; border-collapse: collapse; color: #ffffff; padding: 0 15px 0 16px; height: 5px; line-height: 5px; background-color: #ffffff; border-top: 0; border-left: 1px solid #cccccc; border-bottom: 1px solid #cccccc; border-right: 1px solid #cccccc; border-bottom-right-radius: 5px; border-bottom-left-radius: 5px; mso-line-height-rule: exactly" height="5" bgcolor="#ffffff">&nbsp;</td> 
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                    <td id="footer-pattern" style="padding: 0; border-collapse: collapse; padding: 12px 20px"> 
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                                    <td id="footer-pattern-mobile-separated-links" class="mobile-resize-text" width="100%" colspan="2" style="padding: 0; border-collapse: collapse; color: #999999; font-size: 12px; line-height: 18px; font-family: Arial, sans-serif; mso-line-height-rule: exactly; mso-text-raise: 2px"> Get Jira notifications on your phone! Download the Jira Cloud app for <a href="https://play.google.com/store/apps/details?id=com.atlassian.android.jira.core&referrer=utm_source%3DNotificationLink%26utm_medium%3DEmail" style="color: #3b73af; text-decoration: none">Android</a> or <a href="https://itunes.apple.com/app/apple-store/id1006972087?pt=696495&ct=EmailNotificationLink&mt=8" style="color: #3b73af; text-decoration: none">iOS</a> 
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                                    <td id="footer-pattern-text" class="mobile-resize-text" width="100%" style="padding: 0; border-collapse: collapse; color: #999999; font-size: 12px; line-height: 18px; font-family: Arial, sans-serif; mso-line-height-rule: exactly; mso-text-raise: 2px"> This message was sent by Atlassian Jira <span id="footer-build-information">(v1001.0.0-SNAPSHOT#100130-<span title="10d2092139cf8e207b4f21fcb6dd1d7de337d6a7" data-commit-id="10d2092139cf8e207b4f21fcb6dd1d7de337d6a7}">sha1:10d2092</span>)</span> </td> 
                                    <td id="footer-pattern-logo-desktop-container" valign="top" style="padding: 0; border-collapse: collapse; padding-left: 20px; vertical-align: top"> 
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                                                    <td id="footer-pattern-logo-desktop-padding" style="padding: 0; border-collapse: collapse; padding-top: 3px; opacity: 0.150"> <img id="footer-pattern-logo-desktop" src="cid:jira-generated-image-static-footer-desktop-logo-914b0afa-ad12-494a-96cc-40eb5909b419" alt="Atlassian logo" title="Atlassian logo" width="192" height="24" class="image_fix"> </td> 
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