diff --git a/addons/mail/static/src/core/message_model.js b/addons/mail/static/src/core/message_model.js
index d91a0ca3007..ede580940ee 100644
--- a/addons/mail/static/src/core/message_model.js
+++ b/addons/mail/static/src/core/message_model.js
@@ -187,6 +187,25 @@ export class Message {
         );
     }
 
+    /**
+     * Determines if the link preview is actually the main content of the
+     * message. Meaning:
+     * - The link is the only part of the message body.
+     * - There is only one link in the message body.
+     * - The link preview is of image type.
+     */
+    get linkPreviewSquash() {
+        return (
+            this._store.hasLinkPreviewFeature &&
+            this.body &&
+            this.body.startsWith("<a") &&
+            this.body.endsWith("/a>") &&
+            this.body.match(/<\/a>/im)?.length === 1 &&
+            this.linkPreviews.length === 1 &&
+            this.linkPreviews[0].isImage
+        );
+    }
+
     get inlineBody() {
         if (!this.body) {
             return "";
diff --git a/addons/mail/static/src/core_ui/link_preview/link_preview.scss b/addons/mail/static/src/core_ui/link_preview/link_preview.scss
index b4337ad2724..20365675b7c 100644
--- a/addons/mail/static/src/core_ui/link_preview/link_preview.scss
+++ b/addons/mail/static/src/core_ui/link_preview/link_preview.scss
@@ -17,7 +17,11 @@
 
 .o-mail-LinkPreviewImage img {
     max-height: $o-mail-LinkPreview-height;
-    max-width: Min($o-mail-LinkPreview-width, 100%);
+    max-width: $o-mail-LinkPreview-width;
+}
+
+.o-mail-ChatWindow-content .o-mail-LinkPreviewImage img {
+    max-width: 100%;
 }
 
 .o-mail-LinkPreviewVideo {
diff --git a/addons/mail/static/src/core_ui/message.xml b/addons/mail/static/src/core_ui/message.xml
index fb9a801e8f6..faadc33b892 100644
--- a/addons/mail/static/src/core_ui/message.xml
+++ b/addons/mail/static/src/core_ui/message.xml
@@ -94,21 +94,24 @@
                         >
                             <div t-if="!state.isEditing" class="o-mail-Message-content position-relative" t-att-class="{'d-flex': env.inDiscussApp}">
                                 <t t-if="message.type !== 'notification' and !message.isTransient and (!message.isBodyEmpty or message.subtypeDescription)">
-                                    <div class="position-relative">
-                                        <div class="o-mail-Message-bubble rounded-bottom-3 position-absolute top-0 start-0 w-100 h-100" t-att-class="{
-                                                    'bg-info-light border border-info opacity-25': !message.isSelfAuthored and !message.isNote,
-                                                    'bg-success-light border border-success opacity-25': message.isSelfAuthored and !message.isNote,
-                                                    }" t-attf-class="{{ isAlignedRight ? 'rounded-start-3' : 'rounded-end-3' }}"/>
-                                        <div class="position-relative" t-att-class="{
-                                                    'p-1': message.isNote,
-                                                    'o-mail-Message-body align-self-start text-break mb-0 rounded-end-3 rounded-bottom-3 p-3': !message.isNote,
-                                                    'flex-grow-1': state.isEditing,
-                                                    }" t-ref="body">
-                                            <em t-if="message.subject and !message.isSubjectSimilarToOriginThreadName and !message.isSubjectDefault" class="mb-1 me-2">Subject: <t t-esc="message.subject"/></em>
-                                            <t t-if="message.body" t-out="message.body"/>
-                                            <t t-if="showSubtypeDescription" t-out="message.subtypeDescription"/>
+                                    <t t-if="!message.linkPreviewSquash">
+                                        <div class="position-relative">
+                                            <div class="o-mail-Message-bubble rounded-bottom-3 position-absolute top-0 start-0 w-100 h-100" t-att-class="{
+                                                        'bg-info-light border border-info opacity-25': !message.isSelfAuthored and !message.isNote,
+                                                        'bg-success-light border border-success opacity-25': message.isSelfAuthored and !message.isNote,
+                                                        }" t-attf-class="{{ isAlignedRight ? 'rounded-start-3' : 'rounded-end-3' }}"/>
+                                            <div class="position-relative" t-att-class="{
+                                                        'p-1': message.isNote,
+                                                        'o-mail-Message-body align-self-start text-break mb-0 rounded-end-3 rounded-bottom-3 p-3': !message.isNote,
+                                                        'flex-grow-1': state.isEditing,
+                                                        }" t-ref="body">
+                                                <em t-if="message.subject and !message.isSubjectSimilarToOriginThreadName and !message.isSubjectDefault" class="mb-1 me-2">Subject: <t t-esc="message.subject"/></em>
+                                                <t t-if="message.body" t-out="message.body"/>
+                                                <t t-if="showSubtypeDescription" t-out="message.subtypeDescription"/>
+                                            </div>
                                         </div>
-                                    </div>
+                                    </t>
+                                    <LinkPreviewList t-else="" linkPreviews="message.linkPreviews" deletable="false"/>
                                 </t>
 
                             </div>
@@ -167,7 +170,7 @@
                             attachments="message.attachments"
                             unlinkAttachment.bind="onClickAttachmentUnlink"
                             imagesHeight="300"/>
-                        <LinkPreviewList t-if="message.linkPreviews.length > 0 and store.hasLinkPreviewFeature" linkPreviews="message.linkPreviews" deletable="deletable"/>
+                        <LinkPreviewList t-if="message.linkPreviews.length > 0 and store.hasLinkPreviewFeature and !message.linkPreviewSquash" linkPreviews="message.linkPreviews" deletable="deletable"/>
                         <MessageReactions message="message" openReactionMenu="openReactionMenu" t-if="message.reactions.length"/>
                     </div>
                 </div>
diff --git a/addons/mail/static/tests/message/link_preview_test.js b/addons/mail/static/tests/message/link_preview_test.js
index b7346333e64..cd70ec1284f 100644
--- a/addons/mail/static/tests/message/link_preview_test.js
+++ b/addons/mail/static/tests/message/link_preview_test.js
@@ -262,3 +262,73 @@ QUnit.test("No crash on receiving link preview of non-known message", async (ass
     await nextAnimationFrame();
     assert.ok(true);
 });
+
+QUnit.test(
+    "Squash the message and the link preview when the link preview is an image and the link is the only text in the message",
+    async (assert) => {
+        const pyEnv = await startServer();
+        const linkPreviewId = pyEnv["mail.link.preview"].create({
+            image_mimetype: "image/jpg",
+            source_url:
+                "https://upload.wikimedia.org/wikipedia/commons/thumb/4/41/Siberischer_tiger_de_edit02.jpg/290px-Siberischer_tiger_de_edit02.jpg",
+        });
+        const channelId = pyEnv["mail.channel"].create({ name: "wololo" });
+        pyEnv["mail.message"].create({
+            body: "<a href='linkPreviewLink'>http://linkPreview</a>",
+            link_preview_ids: [linkPreviewId],
+            message_type: "comment",
+            model: "mail.channel",
+            res_id: channelId,
+        });
+        const { openDiscuss } = await start();
+        await openDiscuss(channelId);
+        assert.containsNone($, ".o-mail-Message-bubble");
+    }
+);
+
+QUnit.test(
+    "Link preview and message should not be squashed when the link preview is not an image",
+    async (assert) => {
+        const pyEnv = await startServer();
+        const linkPreviewId = pyEnv["mail.link.preview"].create({
+            og_description: "Description",
+            og_title: "Article title",
+            og_type: "article",
+            source_url: "https://www.odoo.com",
+        });
+        const channelId = pyEnv["mail.channel"].create({ name: "wololo" });
+        pyEnv["mail.message"].create({
+            body: "<a href='linkPreviewLink'>http://linkPreview</a>",
+            link_preview_ids: [linkPreviewId],
+            message_type: "comment",
+            model: "mail.channel",
+            res_id: channelId,
+        });
+        const { openDiscuss } = await start();
+        await openDiscuss(channelId);
+        assert.containsOnce($, ".o-mail-Message-bubble");
+    }
+);
+
+QUnit.test(
+    "Link preview and message should not be squashed when there is more than the link in the message",
+    async (assert) => {
+        const pyEnv = await startServer();
+        const linkPreviewId = pyEnv["mail.link.preview"].create({
+            image_mimetype: "image/jpg",
+            source_url:
+                "https://upload.wikimedia.org/wikipedia/commons/thumb/4/41/Siberischer_tiger_de_edit02.jpg/290px-Siberischer_tiger_de_edit02.jpg",
+        });
+        const channelId = pyEnv["mail.channel"].create({ name: "wololo" });
+        pyEnv["mail.message"].create({
+            body: "<a href='linkPreviewLink'>http://linkPreview</a> not empty",
+            link_preview_ids: [linkPreviewId],
+            message_type: "comment",
+            model: "mail.channel",
+            res_id: channelId,
+        });
+        const { openDiscuss } = await start();
+        await openDiscuss(channelId);
+        assert.containsOnce($, ".o-mail-Message-bubble");
+    }
+);