diff --git a/internal/webserver/handler_messages.go b/internal/webserver/handler_messages.go
index e2c9ca5..22cc05b 100644
--- a/internal/webserver/handler_messages.go
+++ b/internal/webserver/handler_messages.go
@@ -56,11 +56,17 @@ func (app *Application) message_send(w http.ResponseWriter, r *http.Request) {
 	body, err := io.ReadAll(r.Body)
 	panic_if(err)
 	var message_data struct {
-		Text string `json:"text"`
+		Text        string `json:"text"`
+		InReplyToID string `json:"in_reply_to_id"`
 	}
 	panic_if(json.Unmarshal(body, &message_data))
 
-	trove := scraper.SendDMMessage(room_id, message_data.Text, 0)
+	in_reply_to_id, err := strconv.Atoi(message_data.InReplyToID)
+	if err != nil {
+		in_reply_to_id = 0
+	}
+
+	trove := scraper.SendDMMessage(room_id, message_data.Text, scraper.DMMessageID(in_reply_to_id))
 	app.Profile.SaveTweetTrove(trove, false)
 	go app.Profile.SaveTweetTrove(trove, true)
 }
diff --git a/internal/webserver/static/styles.css b/internal/webserver/static/styles.css
index d33157a..3f35432 100644
--- a/internal/webserver/static/styles.css
+++ b/internal/webserver/static/styles.css
@@ -1332,7 +1332,7 @@ main {
 			flex-direction: row-reverse;
 		}
 
-		.dm-message__emoji-button-container {
+		.dm-message__button-container {
 			display: flex;
 			flex-direction: column;
 			justify-content: center;
@@ -1356,30 +1356,7 @@ main {
 			align-items: flex-end;
 		}
 	}
-	.dm-message__replying-to {
-		background-color: #f0f0f0f0;
-		border-radius: 1em 1em 1em 0em;
-		padding: 0.5em 1.2em 2em 1.2em;
-		margin: 0 0 -2em 0.2em;
-		font-size: 0.9em;
 
-		.our-message & {
-			border-radius: 1em 1em 0em 1em;
-			margin: 0 0.2em -2em;
-		}
-
-		.replying-to-message {
-			cursor: pointer;
-		}
-	}
-	.dm-message__replying-to-label {
-		font-size: 0.8em;
-		color: var(--color-twitter-text-gray);
-
-		& img.svg-icon {
-			width: 1em;
-		}
-	}
 	.dm-message__tweet-preview {
 		border-radius: 1em;
 		overflow: hidden; /* TODO: redundancy check-- why is this necessary?  check .rounded-gray-outline */
@@ -1446,18 +1423,43 @@ main {
 	}
 }
 
+.dm-replying-to {
+	background-color: #f0f0f0f0;
+	border-radius: 1em 1em 1em 0em;
+	padding: 0.5em 1.2em 2em 1.2em;
+	margin: 0 0 -2em 0.2em;
+	font-size: 0.9em;
+
+	.our-message & {
+		border-radius: 1em 1em 0em 1em;
+		margin: 0 0.2em -2em;
+	}
+
+	.dm-replying-to__label {
+		font-size: 0.8em;
+		color: var(--color-twitter-text-gray);
+
+		& img.svg-icon {
+			width: 1em;
+		}
+	}
+
+	.dm-replying-to__preview-text {
+		cursor: pointer;
+	}
+}
+
 /**
  * Messages page DM composer module
  */
 .dm-composer {
-	padding-top: 0.5em;
-	border-top: 1px solid var(--color-outline-gray);
-
 	& form {
 		display: flex;
 		gap: 1em;
-		padding: 0.5em 1em;
+		padding: 0.8em 1em;
 		align-items: center;
+		border-top: 1px solid var(--color-outline-gray);
+		background-color: white;
 	}
 	[role="textbox"] {
 		flex-grow: 1;
@@ -1478,4 +1480,22 @@ main {
 		height: 3em;
 		width: 6em;
 	}
+
+
+	.dm-composer__replying-to-container {
+		display: none;
+		&.unhidden {
+			display: revert;
+		}
+
+		/* This is gross; it's to counter the left margin on `dm-replying-to`, which is meant for the one on DMs specifically */
+		margin-left: -0.2em;
+
+		.dm-composer__replying-to {
+			position: absolute;
+			top: 0;
+			transform: translate(0, -100%);
+			width: 100%;
+		}
+	}
 }
diff --git a/internal/webserver/tpl/tweet_page_includes/chat_view.tpl b/internal/webserver/tpl/tweet_page_includes/chat_view.tpl
index 6209538..d4ff37f 100644
--- a/internal/webserver/tpl/tweet_page_includes/chat_view.tpl
+++ b/internal/webserver/tpl/tweet_page_includes/chat_view.tpl
@@ -8,14 +8,14 @@
       </div>
       <div class="dm-message__contents">
         {{if (ne .InReplyToID 0)}}
-          <div class="dm-message__replying-to">
-            <div class="dm-message__replying-to-label labelled-icon">
+          <div class="dm-replying-to">
+            <div class="dm-replying-to__label labelled-icon">
               <img class="svg-icon" src="/static/icons/replying_to.svg" width="24" height="24" />
               <label>Replying to</label>
             </div>
-            <div class="replying-to-message"
+            <div class="dm-replying-to__preview-text"
               data-replying-to-message-id="{{ .InReplyToID }}"
-              onclick="doReplyTo(this)"
+              onclick="handleReplyingToClicked(this)"
             >
               {{(dm_message .InReplyToID).Text}}
             </div>
@@ -65,16 +65,21 @@
           </div>
         {{end}}
       </div>
-      <div class="dm-message__emoji-button-container">
-        <div class="dm-message__emoji-button button" onclick="
-          show_emoji_picker(function(emoji_info) {
-            htmx.ajax('POST', '/messages/{{$.DMChatRoomID}}/reacc', {values: {
-              message_id: '{{$.ID}}',
-              reacc: emoji_info.unicode,
-            }, source: '[data-message-id=\'{{$.ID}}\']'});
-          });
-        ">
-          <img class="svg-icon" src="/static/icons/emoji-react.svg" width="24" height="24"/>
+      <div class="dm-message__button-container">
+        <div class="row">
+          <div class="dm-message__emoji-button button" onclick="
+            show_emoji_picker(function(emoji_info) {
+              htmx.ajax('POST', '/messages/{{$.DMChatRoomID}}/reacc', {values: {
+                message_id: '{{$.ID}}',
+                reacc: emoji_info.unicode,
+              }, source: '[data-message-id=\'{{$.ID}}\']'});
+            });
+          ">
+            <img class="svg-icon" src="/static/icons/emoji-react.svg" width="24" height="24"/>
+          </div>
+          <div class="dm-message__emoji-button button" onclick="handle_reply_clicked(this.closest('.dm-message').getAttribute('data-message-id'))">
+            <img class="svg-icon" src="/static/icons/replying_to.svg" width="24" height="24"/>
+          </div>
         </div>
       </div>
     </div>
@@ -166,12 +171,31 @@
     </div>
     {{if .ActiveRoomID}}
       <div class="dm-composer">
+        {{/* TODO: replying-to CSS re-use is a mess */}}
+        <div id="composerReplyingTo" class="dm-composer__replying-to-container">
+          <div class="dm-replying-to row row--spread">
+            <div>
+              <div class="dm-replying-to__label labelled-icon">
+                <img class="svg-icon" src="/static/icons/replying_to.svg" width="24" height="24" />
+                <label>Replying to</label>
+              </div>
+              <div class="dm-replying-to__preview-text"
+                data-replying-to-message-id=""
+                onclick="handleReplyingToClicked(this)"
+              >
+                Lorem ipsum dolor sit amet
+              </div>
+            </div>
+            <img class="svg-icon button" src="/static/icons/close.svg" width="24" height="24" onclick="cancel_reply()">
+          </div>
+        </div>
+
         <form
           hx-post="/messages/{{.ActiveRoomID}}/send?latest_timestamp={{.LatestPollingTimestamp}}"
           hx-target="#new-messages-poller"
           hx-swap="outerHTML scroll:.chat-messages:bottom"
           hx-ext="json-enc"
-          hx-on:htmx:after-request="composer.innerText = ''; realInput.value = ''; "
+          hx-on:htmx:after-request="composer.innerText = ''; realInput.value = ''; cancel_reply();"
         >
           <img class="svg-icon button" src="/static/icons/emoji-insert.svg" width="24" height="24" onclick="
             var carat = composer.innerText.length;
@@ -192,11 +216,14 @@
           "/>
           <span id="composer" role="textbox" contenteditable oninput="realInput.value = this.innerText"></span>
           <input id="realInput" type="hidden" name="text" value="" />
+          <input id="inReplyToInput" type="hidden" name="in_reply_to_id" value="" />
           <input type="submit" />
         </form>
       </div>
       <script>
-        // Make pasting text work for HTML as well as plain text
+        /**
+         *  Make pasting text work for HTML as well as plain text
+         */
         composer.addEventListener("paste", function(e) {
           // cancel paste
           e.preventDefault();
@@ -205,6 +232,27 @@
           // insert text manually
           document.execCommand("insertHTML", false, text);
         });
+
+        /**
+         * Handle "Reply" button
+         */
+        function handle_reply_clicked(reply_to_message_id) {
+          composerReplyingTo.classList.add("unhidden");
+          inReplyToInput.value = reply_to_message_id;
+          console.log(reply_to_message_id);
+          const message_text_element = document.querySelector('[data-message-id="' + reply_to_message_id + '"] .dm-message__text-content');
+          const preview_text = message_text_element.innerText;
+          const preview_element = composerReplyingTo.querySelector('.dm-replying-to__preview-text');
+          preview_element.innerText = preview_text;
+          preview_element.setAttribute("data-replying-to-message-id", reply_to_message_id);
+        }
+        /**
+         * Handle cancel-reply button
+         */
+        function cancel_reply() {
+          composerReplyingTo.classList.remove("unhidden");
+          inReplyToInput.value = "";
+        }
       </script>
 
       {{ $room := (index $.Rooms $.ActiveRoomID) }}
@@ -265,7 +313,7 @@
      * Define callback on-click handler for 'replying-to' previews; they should scroll the replied-to
      * message into view, if possible.
      */
-    function doReplyTo(replying_to_box) {
+    function handleReplyingToClicked(replying_to_box) {
       const replied_to_id = replying_to_box.getAttribute("data-replying-to-message-id");
       const replied_to_message = document.querySelector('[data-message-id="' + replied_to_id + '"]');