diff --git a/app/post_metadata.go b/app/post_metadata.go
index b2868330da..5c14646410 100644
--- a/app/post_metadata.go
+++ b/app/post_metadata.go
@@ -486,6 +486,14 @@ func looksLikeAPermalink(url, siteURL string) bool {
 	return matched
 }
 
+func (a *App) containsPermalink(post *model.Post) bool {
+	link, _ := a.getFirstLinkAndImages(post.Message)
+	if link == "" {
+		return false
+	}
+	return looksLikeAPermalink(link, a.GetSiteURL())
+}
+
 func (a *App) getLinkMetadata(requestURL string, timestamp int64, isNewPost bool, previewedPostPropVal string) (*opengraph.OpenGraph, *model.PostImage, *model.Permalink, error) {
 	requestURL = resolveMetadataURL(requestURL, a.GetSiteURL())
 
@@ -530,7 +538,15 @@ func (a *App) getLinkMetadata(requestURL string, timestamp int64, isNewPost bool
 			return nil, nil, nil, appErr
 		}
 
-		permalink = &model.Permalink{PreviewPost: model.NewPreviewPost(referencedPost, referencedTeam, referencedChannel)}
+		// Get metadata for embedded post
+		if a.containsPermalink(referencedPost) {
+			// referencedPost contains a permalink: we don't get its metadata
+			permalink = &model.Permalink{PreviewPost: model.NewPreviewPost(referencedPost, referencedTeam, referencedChannel)}
+		} else {
+			// referencedPost does not contain a permalink: we get its metadata
+			referencedPostWithMetadata := a.PreparePostForClientWithEmbedsAndImages(referencedPost, false, false)
+			permalink = &model.Permalink{PreviewPost: model.NewPreviewPost(referencedPostWithMetadata, referencedTeam, referencedChannel)}
+		}
 	} else {
 
 		var request *http.Request
diff --git a/app/post_metadata_test.go b/app/post_metadata_test.go
index 8a96604763..08500f90bb 100644
--- a/app/post_metadata_test.go
+++ b/app/post_metadata_test.go
@@ -585,6 +585,90 @@ func TestPreparePostForClient(t *testing.T) {
 		require.Equal(t, referencedPost.Id, preview.PostID)
 	})
 
+	t.Run("permalink with nested preview should have referenced post metadata", func(t *testing.T) {
+		th := setup(t)
+		defer th.TearDown()
+
+		th.App.UpdateConfig(func(cfg *model.Config) {
+			*cfg.ServiceSettings.SiteURL = "http://mymattermost.com"
+		})
+
+		th.Context.Session().UserId = th.BasicUser.Id
+
+		referencedPost, err := th.App.CreatePost(th.Context, &model.Post{
+			UserId:    th.BasicUser.Id,
+			ChannelId: th.BasicChannel.Id,
+			Message:   `This is our logo: ` + server.URL + `/test-image2.png`,
+		}, th.BasicChannel, false, true)
+		require.Nil(t, err)
+		referencedPost.Metadata.Embeds = nil
+
+		link := fmt.Sprintf("%s/%s/pl/%s", *th.App.Config().ServiceSettings.SiteURL, th.BasicTeam.Name, referencedPost.Id)
+
+		previewPost, err := th.App.CreatePost(th.Context, &model.Post{
+			UserId:    th.BasicUser.Id,
+			ChannelId: th.BasicChannel.Id,
+			Message:   link,
+		}, th.BasicChannel, false, true)
+		require.Nil(t, err)
+		previewPost.Metadata.Embeds = nil
+
+		clientPost := th.App.PreparePostForClientWithEmbedsAndImages(previewPost, false, false)
+		firstEmbed := clientPost.Metadata.Embeds[0]
+		preview := firstEmbed.Data.(*model.PreviewPost)
+		referencedPostFirstEmbed := preview.Post.Metadata.Embeds[0]
+
+		require.Equal(t, referencedPost.Id, preview.PostID)
+		require.Equal(t, referencedPostFirstEmbed.URL, serverURL+`/test-image2.png`)
+	})
+
+	t.Run("permalink with nested permalink should not have referenced post metadata", func(t *testing.T) {
+		th := setup(t)
+		defer th.TearDown()
+
+		th.App.UpdateConfig(func(cfg *model.Config) {
+			*cfg.ServiceSettings.SiteURL = "http://mymattermost.com"
+		})
+
+		th.Context.Session().UserId = th.BasicUser.Id
+
+		nestedPermalinkPost, err := th.App.CreatePost(th.Context, &model.Post{
+			UserId:    th.BasicUser.Id,
+			ChannelId: th.BasicChannel.Id,
+			Message:   `This is our logo: ` + server.URL + `/test-image2.png`,
+		}, th.BasicChannel, false, true)
+		require.Nil(t, err)
+		nestedPermalinkPost.Metadata.Embeds = nil
+
+		nestedLink := fmt.Sprintf("%s/%s/pl/%s", *th.App.Config().ServiceSettings.SiteURL, th.BasicTeam.Name, nestedPermalinkPost.Id)
+
+		referencedPost, err := th.App.CreatePost(th.Context, &model.Post{
+			UserId:    th.BasicUser.Id,
+			ChannelId: th.BasicChannel.Id,
+			Message:   nestedLink,
+		}, th.BasicChannel, false, true)
+		require.Nil(t, err)
+		referencedPost.Metadata.Embeds = nil
+
+		link := fmt.Sprintf("%s/%s/pl/%s", *th.App.Config().ServiceSettings.SiteURL, th.BasicTeam.Name, referencedPost.Id)
+
+		previewPost, err := th.App.CreatePost(th.Context, &model.Post{
+			UserId:    th.BasicUser.Id,
+			ChannelId: th.BasicChannel.Id,
+			Message:   link,
+		}, th.BasicChannel, false, true)
+		require.Nil(t, err)
+		previewPost.Metadata.Embeds = nil
+
+		clientPost := th.App.PreparePostForClientWithEmbedsAndImages(previewPost, false, false)
+		firstEmbed := clientPost.Metadata.Embeds[0]
+		preview := firstEmbed.Data.(*model.PreviewPost)
+		referencedPostMetadata := preview.Post.Metadata
+
+		require.Equal(t, referencedPost.Id, preview.PostID)
+		require.Equal(t, referencedPostMetadata, (*model.PostMetadata)(nil))
+	})
+
 	t.Run("permalink preview renders after toggling off the feature", func(t *testing.T) {
 		th := setup(t)
 		defer th.TearDown()
@@ -2482,3 +2566,39 @@ func TestLooksLikeAPermalink(t *testing.T) {
 		})
 	}
 }
+
+func TestContainsPermalink(t *testing.T) {
+	th := Setup(t)
+	defer th.TearDown()
+
+	const siteURLWithSubpath = "http://localhost:8065/foo"
+
+	testCases := []struct {
+		Description string
+		Post        *model.Post
+		Expected    bool
+	}{
+		{
+			Description: "contains a permalink",
+			Post: &model.Post{
+				Message: fmt.Sprintf("%s/private-core/pl/dppezk51jp8afbhwxf1jpag66r", siteURLWithSubpath),
+			},
+			Expected: true,
+		},
+		{
+			Description: "does not contain a permalink",
+			Post: &model.Post{
+				Message: "foobar",
+			},
+			Expected: false,
+		},
+	}
+
+	for _, testCase := range testCases {
+		testCase := testCase
+		t.Run(testCase.Description, func(t *testing.T) {
+			actual := th.App.containsPermalink(testCase.Post)
+			assert.Equal(t, testCase.Expected, actual)
+		})
+	}
+}