diff --git a/web/src/compose_actions.js b/web/src/compose_actions.js
index b516af5e59..ec74a5aa98 100644
--- a/web/src/compose_actions.js
+++ b/web/src/compose_actions.js
@@ -536,25 +536,17 @@ export function quote_and_reply(opts) {
     const message = message_lists.current.selected_message();
     const quoting_placeholder = $t({defaultMessage: "[Quoting…]"});
 
-    if (compose_state.has_message_content()) {
-        // The user already started typing a message,
-        // so we won't re-open the compose box.
+    if (!compose_state.has_message_content()) {
+        // The user has not started typing a message,
+        // so we will re-open the compose box.
         // (If you did re-open the compose box, you
         // are prone to glitches where you select the
         // text, plus it's a complicated codepath that
         // can have other unintended consequences.)
-
-        if ($textarea.caret() !== 0) {
-            // Insert a newline before quoted message if there is
-            // already some content in the compose box and quoted
-            // message is not being inserted at the beginning.
-            $textarea.caret("\n");
-        }
-    } else {
         respond_to_message(opts);
     }
 
-    compose_ui.insert_syntax_and_focus(quoting_placeholder + "\n", $textarea);
+    compose_ui.insert_syntax_and_focus(quoting_placeholder, $textarea, "block");
 
     function replace_content(message) {
         // Final message looks like:
diff --git a/web/src/compose_ui.js b/web/src/compose_ui.js
index 8e7ca68cb5..14e84fe19a 100644
--- a/web/src/compose_ui.js
+++ b/web/src/compose_ui.js
@@ -30,7 +30,7 @@ export function autosize_textarea($textarea) {
     }
 }
 
-export function smart_insert($textarea, syntax) {
+export function smart_insert_inline($textarea, syntax) {
     function is_space(c) {
         return c === " " || c === "\t" || c === "\n";
     }
@@ -68,11 +68,69 @@ export function smart_insert($textarea, syntax) {
     autosize_textarea($textarea);
 }
 
-export function insert_syntax_and_focus(syntax, $textarea = $("#compose-textarea")) {
+export function smart_insert_block($textarea, syntax) {
+    const pos = $textarea.caret();
+    const before_str = $textarea.val().slice(0, pos);
+    const after_str = $textarea.val().slice(pos);
+
+    if (pos > 0) {
+        // Insert newline/s before the content block if there is
+        // already some content in the compose box and the content
+        // block is not being inserted at the beginning, such
+        // that there are at least 2 new lines between the content
+        // and start of the content block.
+        let new_lines_before_count = 0;
+        let current_pos = pos - 1;
+        while (
+            current_pos >= 0 &&
+            before_str.charAt(current_pos) === "\n" &&
+            new_lines_before_count < 2
+        ) {
+            // count up to 2 new lines before cursor
+            current_pos -= 1;
+            new_lines_before_count += 1;
+        }
+        const new_lines_needed_before_count = 2 - new_lines_before_count;
+        syntax = "\n".repeat(new_lines_needed_before_count) + syntax;
+    }
+
+    let new_lines_after_count = 0;
+    let current_pos = 0;
+    while (
+        current_pos < after_str.length &&
+        after_str.charAt(current_pos) === "\n" &&
+        new_lines_after_count < 2
+    ) {
+        // count up to 2 new lines after cursor
+        current_pos += 1;
+        new_lines_after_count += 1;
+    }
+    // Insert newline/s after the content block, such that there
+    // are at least 2 new lines between the content block and
+    // the content after the cursor, if any.
+    const new_lines_needed_after_count = 2 - new_lines_after_count;
+    syntax = syntax + "\n".repeat(new_lines_needed_after_count);
+
+    // text-field-edit ensures `$textarea` is focused before inserting
+    // the new syntax.
+    insert($textarea[0], syntax);
+
+    autosize_textarea($textarea);
+}
+
+export function insert_syntax_and_focus(
+    syntax,
+    $textarea = $("#compose-textarea"),
+    mode = "inline",
+) {
     // Generic helper for inserting syntax into the main compose box
     // where the cursor was and focusing the area.  Mostly a thin
-    // wrapper around smart_insert.
-    smart_insert($textarea, syntax);
+    // wrapper around smart_insert_inline and smart_inline_block.
+    if (mode === "inline") {
+        smart_insert_inline($textarea, syntax);
+    } else if (mode === "block") {
+        smart_insert_block($textarea, syntax);
+    }
 }
 
 export function replace_syntax(old_syntax, new_syntax, $textarea = $("#compose-textarea")) {
diff --git a/web/tests/compose_actions.test.js b/web/tests/compose_actions.test.js
index 234734bf78..d4fd72c229 100644
--- a/web/tests/compose_actions.test.js
+++ b/web/tests/compose_actions.test.js
@@ -359,8 +359,9 @@ test("quote_and_reply", ({disallow, override, override_rewire}) => {
 
     override(message_lists.current, "selected_id", () => 100);
 
-    override(compose_ui, "insert_syntax_and_focus", (syntax) => {
-        assert.equal(syntax, "translated: [Quoting…]\n");
+    override(compose_ui, "insert_syntax_and_focus", (syntax, $textarea, mode) => {
+        assert.equal(syntax, "translated: [Quoting…]");
+        assert.equal(mode, "block");
     });
 
     const opts = {
diff --git a/web/tests/compose_ui.test.js b/web/tests/compose_ui.test.js
index 398ca8018b..2992e77302 100644
--- a/web/tests/compose_ui.test.js
+++ b/web/tests/compose_ui.test.js
@@ -120,34 +120,34 @@ run_test("smart_insert", ({override}) => {
         });
     }
     override_with_expected_syntax(" :smile: ");
-    compose_ui.smart_insert($textbox, ":smile:");
+    compose_ui.smart_insert_inline($textbox, ":smile:");
 
     override_with_expected_syntax(" :airplane: ");
-    compose_ui.smart_insert($textbox, ":airplane:");
+    compose_ui.smart_insert_inline($textbox, ":airplane:");
 
     $textbox.caret(0);
     override_with_expected_syntax(":octopus: ");
-    compose_ui.smart_insert($textbox, ":octopus:");
+    compose_ui.smart_insert_inline($textbox, ":octopus:");
 
     $textbox.caret($textbox.val().length);
     override_with_expected_syntax(" :heart: ");
-    compose_ui.smart_insert($textbox, ":heart:");
+    compose_ui.smart_insert_inline($textbox, ":heart:");
 
     // Test handling of spaces for ```quote
     $textbox = make_textbox("");
     $textbox.caret(0);
-    override_with_expected_syntax("```quote\nquoted message\n```\n");
-    compose_ui.smart_insert($textbox, "```quote\nquoted message\n```\n");
+    override_with_expected_syntax("```quote\nquoted message\n```\n\n");
+    compose_ui.smart_insert_block($textbox, "```quote\nquoted message\n```");
 
     $textbox = make_textbox("");
     $textbox.caret(0);
-    override_with_expected_syntax("translated: [Quoting…]\n");
-    compose_ui.smart_insert($textbox, "translated: [Quoting…]\n");
+    override_with_expected_syntax("translated: [Quoting…]\n\n");
+    compose_ui.smart_insert_block($textbox, "translated: [Quoting…]");
 
     $textbox = make_textbox("abc");
     $textbox.caret(3);
-    override_with_expected_syntax(" test with space ");
-    compose_ui.smart_insert($textbox, " test with space");
+    override_with_expected_syntax("\n\n test with space\n\n");
+    compose_ui.smart_insert_block($textbox, " test with space");
 
     // Note that we don't have any special logic for strings that are
     // already surrounded by spaces, since we are usually inserting things
@@ -281,23 +281,28 @@ run_test("quote_and_reply", ({override, override_rewire}) => {
             textarea_caret_pos = arg;
             return this;
         }
-        /* istanbul ignore if */
-        if (typeof arg !== "string") {
-            console.info(arg);
-            throw new Error("We expected the actual code to pass in a string.");
+
+        /* This next block of mocking code is currently unused, but
+           is preserved, since it may be useful in the future. */
+        /* istanbul ignore next */
+        {
+            if (typeof arg !== "string") {
+                console.info(arg);
+                throw new Error("We expected the actual code to pass in a string.");
+            }
+
+            const before = textarea_val.slice(0, textarea_caret_pos);
+            const after = textarea_val.slice(textarea_caret_pos);
+
+            textarea_val = before + arg + after;
+            textarea_caret_pos += arg.length;
+            return this;
         }
-
-        const before = textarea_val.slice(0, textarea_caret_pos);
-        const after = textarea_val.slice(textarea_caret_pos);
-
-        textarea_val = before + arg + after;
-        textarea_caret_pos += arg.length;
-        return this;
     };
     $("#compose-textarea")[0] = "compose-textarea";
     override(text_field_edit, "insert", (elt, syntax) => {
         assert.equal(elt, "compose-textarea");
-        assert.equal(syntax, "translated: [Quoting…]\n");
+        assert.equal(syntax, "\n\ntranslated: [Quoting…]\n\n");
     });
 
     function set_compose_content_with_caret(content) {
@@ -343,7 +348,11 @@ run_test("quote_and_reply", ({override, override_rewire}) => {
     reset_test_state();
 
     // If the caret is initially positioned at 0, it should not
-    // add a newline before the quoted message.
+    // add newlines before the quoted message.
+    override(text_field_edit, "insert", (elt, syntax) => {
+        assert.equal(elt, "compose-textarea");
+        assert.equal(syntax, "translated: [Quoting…]\n\n");
+    });
     set_compose_content_with_caret("%hello there");
     compose_actions.quote_and_reply();
 
@@ -387,6 +396,40 @@ run_test("quote_and_reply", ({override, override_rewire}) => {
     success_function({
         raw_content: quote_text,
     });
+
+    reset_test_state();
+
+    // When there is already 1 newline before and after the caret,
+    // only 1 newline is added before and after the quoted message.
+    override(text_field_edit, "insert", (elt, syntax) => {
+        assert.equal(elt, "compose-textarea");
+        assert.equal(syntax, "\ntranslated: [Quoting…]\n");
+    });
+    set_compose_content_with_caret("1st line\n%\n2nd line");
+    compose_actions.quote_and_reply();
+
+    quote_text = "Testing with caret on a new line between 2 lines of text.";
+    override_with_quote_text(quote_text);
+    success_function({
+        raw_content: quote_text,
+    });
+
+    reset_test_state();
+
+    // When there are many (>=2) newlines before and after the caret,
+    // no newline is added before or after the quoted message.
+    override(text_field_edit, "insert", (elt, syntax) => {
+        assert.equal(elt, "compose-textarea");
+        assert.equal(syntax, "translated: [Quoting…]");
+    });
+    set_compose_content_with_caret("lots of\n\n\n\n%\n\n\nnewlines");
+    compose_actions.quote_and_reply();
+
+    quote_text = "Testing with caret on a new line between many empty newlines.";
+    override_with_quote_text(quote_text);
+    success_function({
+        raw_content: quote_text,
+    });
 });
 
 run_test("set_compose_box_top", () => {