diff --git a/src/org/thoughtcrime/securesms/conversation/ConversationActivity.java b/src/org/thoughtcrime/securesms/conversation/ConversationActivity.java
index 88c5404192..8da4fd994e 100644
--- a/src/org/thoughtcrime/securesms/conversation/ConversationActivity.java
+++ b/src/org/thoughtcrime/securesms/conversation/ConversationActivity.java
@@ -152,6 +152,7 @@ import org.thoughtcrime.securesms.jobs.RetrieveProfileJob;
 import org.thoughtcrime.securesms.jobs.ServiceOutageDetectionJob;
 import org.thoughtcrime.securesms.linkpreview.LinkPreview;
 import org.thoughtcrime.securesms.linkpreview.LinkPreviewRepository;
+import org.thoughtcrime.securesms.linkpreview.LinkPreviewUtil;
 import org.thoughtcrime.securesms.linkpreview.LinkPreviewViewModel;
 import org.thoughtcrime.securesms.logging.Log;
 import org.thoughtcrime.securesms.loki.FriendRequestViewDelegate;
@@ -2180,11 +2181,12 @@ public class ConversationActivity extends PassphraseRequiredActionBarActivity
       long            expiresIn      = recipient.getExpireMessages() * 1000L;
       boolean         initiating     = threadId == -1;
       boolean         needsSplit     = !transport.isSms() && message.length() > transport.calculateCharacters(message).maxPrimaryMessageSize;
-      boolean         isMediaMessage = attachmentManager.isAttachmentPresent() ||
-                                       recipient.isGroupRecipient()            ||
-                                       recipient.getAddress().isEmail()        ||
-                                       inputPanel.getQuote().isPresent()       ||
-                                       linkPreviewViewModel.hasLinkPreview()   ||
+      boolean         isMediaMessage = attachmentManager.isAttachmentPresent()        ||
+                                       recipient.isGroupRecipient()                   ||
+                                       recipient.getAddress().isEmail()               ||
+                                       inputPanel.getQuote().isPresent()              ||
+                                       linkPreviewViewModel.hasLinkPreview()          ||
+                                       LinkPreviewUtil.isWhitelistedMediaUrl(message) ||
                                        needsSplit;
 
       Log.i(TAG, "isManual Selection: " + sendButton.isManualSelection());
diff --git a/src/org/thoughtcrime/securesms/jobs/PushGroupSendJob.java b/src/org/thoughtcrime/securesms/jobs/PushGroupSendJob.java
index 92c0827ccd..4d8b3e5775 100644
--- a/src/org/thoughtcrime/securesms/jobs/PushGroupSendJob.java
+++ b/src/org/thoughtcrime/securesms/jobs/PushGroupSendJob.java
@@ -95,7 +95,7 @@ public class PushGroupSendJob extends PushSendJob implements InjectableType {
       OutgoingMediaMessage message     = database.getOutgoingMessage(messageId);
       List<Attachment>     attachments = new LinkedList<>();
 
-      attachments.addAll(message.getAttachments());
+      // attachments.addAll(message.getAttachments());
       // attachments.addAll(Stream.of(message.getLinkPreviews()).filter(p -> p.getThumbnail().isPresent()).map(p -> p.getThumbnail().get()).toList());
       attachments.addAll(Stream.of(message.getSharedContacts()).filter(c -> c.getAvatar() != null).map(c -> c.getAvatar().getAttachment()).withoutNulls().toList());
 
diff --git a/src/org/thoughtcrime/securesms/jobs/PushMediaSendJob.java b/src/org/thoughtcrime/securesms/jobs/PushMediaSendJob.java
index 3f384fff8f..dd39fcb69d 100644
--- a/src/org/thoughtcrime/securesms/jobs/PushMediaSendJob.java
+++ b/src/org/thoughtcrime/securesms/jobs/PushMediaSendJob.java
@@ -76,7 +76,7 @@ public class PushMediaSendJob extends PushSendJob implements InjectableType {
       OutgoingMediaMessage message     = database.getOutgoingMessage(messageId);
       List<Attachment>     attachments = new LinkedList<>();
 
-      attachments.addAll(message.getAttachments());
+      // attachments.addAll(message.getAttachments());
       // attachments.addAll(Stream.of(message.getLinkPreviews()).filter(p -> p.getThumbnail().isPresent()).map(p -> p.getThumbnail().get()).toList());
       attachments.addAll(Stream.of(message.getSharedContacts()).filter(c -> c.getAvatar() != null).map(c -> c.getAvatar().getAttachment()).withoutNulls().toList());
 
diff --git a/src/org/thoughtcrime/securesms/linkpreview/LinkPreviewDomains.java b/src/org/thoughtcrime/securesms/linkpreview/LinkPreviewDomains.java
index 01f56ce798..6e99f84ac9 100644
--- a/src/org/thoughtcrime/securesms/linkpreview/LinkPreviewDomains.java
+++ b/src/org/thoughtcrime/securesms/linkpreview/LinkPreviewDomains.java
@@ -33,7 +33,6 @@ public class LinkPreviewDomains {
       "redd.it",
       "imgur.com",
       "pinimg.com",
-      "giphy.com",
-      "tenor.com"
+      "giphy.com"
   ));
 }
diff --git a/src/org/thoughtcrime/securesms/sms/MessageSender.java b/src/org/thoughtcrime/securesms/sms/MessageSender.java
index df61b4b164..a33ac1d25e 100644
--- a/src/org/thoughtcrime/securesms/sms/MessageSender.java
+++ b/src/org/thoughtcrime/securesms/sms/MessageSender.java
@@ -39,6 +39,8 @@ import org.thoughtcrime.securesms.jobs.PushGroupSendJob;
 import org.thoughtcrime.securesms.jobs.PushMediaSendJob;
 import org.thoughtcrime.securesms.jobs.PushTextSendJob;
 import org.thoughtcrime.securesms.jobs.SmsSendJob;
+import org.thoughtcrime.securesms.linkpreview.LinkPreviewRepository;
+import org.thoughtcrime.securesms.linkpreview.LinkPreviewUtil;
 import org.thoughtcrime.securesms.logging.Log;
 import org.thoughtcrime.securesms.mms.MmsException;
 import org.thoughtcrime.securesms.mms.OutgoingMediaMessage;
@@ -46,6 +48,7 @@ import org.thoughtcrime.securesms.push.AccountManagerFactory;
 import org.thoughtcrime.securesms.recipients.Recipient;
 import org.thoughtcrime.securesms.service.ExpiringMessageManager;
 import org.thoughtcrime.securesms.util.TextSecurePreferences;
+import org.thoughtcrime.securesms.util.Util;
 import org.whispersystems.libsignal.util.guava.Optional;
 import org.whispersystems.signalservice.api.SignalServiceAccountManager;
 import org.whispersystems.signalservice.api.push.ContactTokenDetails;
@@ -93,28 +96,42 @@ public class MessageSender {
                           final boolean forceSms,
                           final SmsDatabase.InsertListener insertListener)
   {
-    try {
-      ThreadDatabase threadDatabase = DatabaseFactory.getThreadDatabase(context);
-      MmsDatabase    database       = DatabaseFactory.getMmsDatabase(context);
+    ThreadDatabase threadDatabase = DatabaseFactory.getThreadDatabase(context);
+    MmsDatabase    database       = DatabaseFactory.getMmsDatabase(context);
 
-      long allocatedThreadId;
+    long allocatedThreadId;
 
-      if (threadId == -1) {
-        allocatedThreadId = threadDatabase.getThreadIdFor(message.getRecipient(), message.getDistributionType());
-      } else {
-        allocatedThreadId = threadId;
-      }
-
-      Recipient recipient = message.getRecipient();
-      long      messageId = database.insertMessageOutbox(message, allocatedThreadId, forceSms, insertListener);
-
-      sendMediaMessage(context, recipient, forceSms, messageId, message.getExpiresIn());
-
-      return allocatedThreadId;
-    } catch (MmsException e) {
-      Log.w(TAG, e);
-      return threadId;
+    if (threadId == -1) {
+      allocatedThreadId = threadDatabase.getThreadIdFor(message.getRecipient(), message.getDistributionType());
+    } else {
+      allocatedThreadId = threadId;
     }
+
+    Recipient recipient = message.getRecipient();
+
+    if (message.getLinkPreviews().isEmpty() && message.getAttachments().isEmpty() && LinkPreviewUtil.isWhitelistedMediaUrl(message.getBody())) {
+      new LinkPreviewRepository(context).fetchGIF(context, message.getBody(), attachmentOrNull -> Util.runOnMain(() -> {
+        if (attachmentOrNull.isPresent()) {
+          Attachment attachment = attachmentOrNull.get();
+          try {
+            message.getAttachments().add(attachment);
+            long messageId = database.insertMessageOutbox(message, allocatedThreadId, forceSms, insertListener);
+            sendMediaMessage(context, recipient, forceSms, messageId, message.getExpiresIn());
+          } catch (Exception e) {
+            // TODO: Handle
+          }
+        } else {
+          try {
+            long messageId = database.insertMessageOutbox(message, allocatedThreadId, forceSms, insertListener);
+            sendMediaMessage(context, recipient, forceSms, messageId, message.getExpiresIn());
+          } catch (MmsException e) {
+            // TODO: Handle
+          }
+        }
+      }));
+    }
+
+    return allocatedThreadId;
   }
 
   public static void resendGroupMessage(Context context, MessageRecord messageRecord, Address filterAddress) {