diff --git a/internal/cmd/compose_test.go b/internal/cmd/compose_test.go
index f8508e62..dee0ad43 100644
--- a/internal/cmd/compose_test.go
+++ b/internal/cmd/compose_test.go
@@ -130,6 +130,19 @@ func TestComposeSendsRawHTMLVerbatim(t *testing.T) {
 	}
 }
 
+func TestComposeKeepsWhitespaceInRawHTML(t *testing.T) {
+	server, sent := threadReplyServer(t, messageAddressedToJane, 11, 12)
+	body := "<pre>first<br>\n second</pre>"
+
+	err := runCLI(t, server, "--account", "8", "compose", "--thread-id", "7", "--message-html", body)
+	if err != nil {
+		t.Fatalf("compose failed: %v", err)
+	}
+	if sent.Content != body {
+		t.Errorf("content = %q, want raw HTML %q", sent.Content, body)
+	}
+}
+
 func TestComposeRefusesMessageAndMessageHTMLTogether(t *testing.T) {
 	server, sent := threadReplyServer(t, messageAddressedToJane, 11, 12)
 
diff --git a/internal/cmd/contacts_test.go b/internal/cmd/contacts_test.go
index 2813883a..75e56a75 100644
--- a/internal/cmd/contacts_test.go
+++ b/internal/cmd/contacts_test.go
@@ -400,7 +400,7 @@ func TestContactNoteSetKeepsLineBreaks(t *testing.T) {
 	if err := json.Unmarshal(requests[0].Body, &body); err != nil {
 		t.Fatal(err)
 	}
-	if want := "<p>First line<br>\nSecond line</p>"; body.Contact.Note != want {
+	if want := "<p>First line<br>Second line</p>"; body.Contact.Note != want {
 		t.Errorf("note = %q, want %q", body.Contact.Note, want)
 	}
 }
diff --git a/internal/cmd/draft_test.go b/internal/cmd/draft_test.go
index e3e3dbcc..3c8ff5a8 100644
--- a/internal/cmd/draft_test.go
+++ b/internal/cmd/draft_test.go
@@ -79,6 +79,23 @@ func TestComposeDraftSavesInsteadOfSending(t *testing.T) {
 	}
 }
 
+func TestComposeDraftStartsEveryWrappedLineFlush(t *testing.T) {
+	var writes []draftWrite
+	_, err := runJSONCommand(t, draftLifecycleServer(t, draftEditJSON, &writes),
+		"compose", "--subject", "A short note", "-m", "AAA.\nBBB.\n\nCCC.", "--draft")
+	if err != nil {
+		t.Fatalf("compose --draft: %v", err)
+	}
+
+	if len(writes) != 1 {
+		t.Fatalf("writes = %+v", writes)
+	}
+	message, _ := writes[0].Body["message"].(map[string]any)
+	if want := "<p>AAA.<br>BBB.</p>\n<p>CCC.</p>"; message["content"] != want {
+		t.Errorf("content = %q, want %q", message["content"], want)
+	}
+}
+
 // A draft needs nobody on it yet — only a send does.
 func TestComposeDraftNeedsNoRecipients(t *testing.T) {
 	var writes []draftWrite
diff --git a/internal/cmd/forward_test.go b/internal/cmd/forward_test.go
index ec05a8c1..7e9ff0b7 100644
--- a/internal/cmd/forward_test.go
+++ b/internal/cmd/forward_test.go
@@ -108,7 +108,7 @@ func TestForwardSendsLatestEntryDraft(t *testing.T) {
 	if sent.Subject != "Fwd: Quarterly planning" {
 		t.Errorf("subject = %q", sent.Subject)
 	}
-	wantContent := "<p>For your review<br>\nThanks &amp; take care</p><br><div>Quoted message</div>"
+	wantContent := "<p>For your review<br>Thanks &amp; take care</p><br><div>Quoted message</div>"
 	if sent.Content != wantContent {
 		t.Errorf("content = %q, want %q", sent.Content, wantContent)
 	}
diff --git a/internal/htmlutil/from_markdown.go b/internal/htmlutil/from_markdown.go
index 6e87fdd5..3313670e 100644
--- a/internal/htmlutil/from_markdown.go
+++ b/internal/htmlutil/from_markdown.go
@@ -21,10 +21,43 @@ var fromMarkdown = goldmark.New(
 	goldmark.WithRendererOptions(
 		htmlrenderer.WithHardWraps(),
 		htmlrenderer.WithUnsafe(),
-		renderer.WithNodeRenderers(util.Prioritized(&trixCodeBlockRenderer{}, 100)),
+		renderer.WithNodeRenderers(
+			util.Prioritized(&trixTextRenderer{}, 100),
+			util.Prioritized(&trixCodeBlockRenderer{}, 100),
+		),
 	),
 )
 
+// trixTextRenderer writes line breaks without formatting whitespace after them, so the
+// next line starts with exactly the text the author wrote. Goldmark's default renderer
+// writes a newline after every <br>, and Trix keeps that newline with the following text.
+type trixTextRenderer struct{}
+
+func (r *trixTextRenderer) RegisterFuncs(reg renderer.NodeRendererFuncRegisterer) {
+	reg.Register(ast.KindText, r.renderText)
+}
+
+func (r *trixTextRenderer) renderText(w util.BufWriter, source []byte, node ast.Node, entering bool) (ast.WalkStatus, error) {
+	if !entering {
+		return ast.WalkContinue, nil
+	}
+	text, ok := node.(*ast.Text)
+	if !ok {
+		return ast.WalkContinue, nil
+	}
+
+	value := text.Segment.Value(source)
+	if text.IsRaw() {
+		htmlrenderer.DefaultWriter.RawWrite(w, value)
+	} else {
+		htmlrenderer.DefaultWriter.Write(w, value)
+		if text.HardLineBreak() || text.SoftLineBreak() {
+			_, _ = w.WriteString("<br>")
+		}
+	}
+	return ast.WalkContinue, nil
+}
+
 // trixLanguages maps a fence's info string to the language names HEY's own code
 // blocks carry, which is the set its server-side highlighter accepts.
 var trixLanguages = map[string]string{
diff --git a/internal/htmlutil/from_markdown_test.go b/internal/htmlutil/from_markdown_test.go
index 5a363e5b..8930c9bf 100644
--- a/internal/htmlutil/from_markdown_test.go
+++ b/internal/htmlutil/from_markdown_test.go
@@ -14,20 +14,60 @@ func TestFromMarkdown(t *testing.T) {
 			want: "<p>Hello there</p>",
 		},
 		{
-			name: "single newline becomes a hard break",
+			name: "single newline becomes a hard break without indenting the next line",
 			md:   "Line one\nLine two",
-			want: "<p>Line one<br>\nLine two</p>",
+			want: "<p>Line one<br>Line two</p>",
 		},
 		{
-			name: "CRLF newline becomes a hard break",
+			name: "CRLF newline becomes a hard break without indenting the next line",
 			md:   "Line one\r\nLine two",
-			want: "<p>Line one<br>\nLine two</p>",
+			want: "<p>Line one<br>Line two</p>",
+		},
+		{
+			name: "every continuation line starts flush",
+			md:   "Line one\nLine two\nLine three",
+			want: "<p>Line one<br>Line two<br>Line three</p>",
+		},
+		{
+			name: "two-space Markdown break starts the next line flush",
+			md:   "Line one  \nLine two",
+			want: "<p>Line one<br>Line two</p>",
+		},
+		{
+			name: "backslash Markdown break starts the next line flush",
+			md:   "Line one\\\nLine two",
+			want: "<p>Line one<br>Line two</p>",
 		},
 		{
 			name: "blank line splits paragraphs",
 			md:   "Para one\n\nPara two",
 			want: "<p>Para one</p>\n<p>Para two</p>",
 		},
+		{
+			name: "wrapped inline markup keeps escaping",
+			md:   "**Bold** & safe\n[HEY](https://hey.com)",
+			want: `<p><strong>Bold</strong> &amp; safe<br><a href="https://hey.com">HEY</a></p>`,
+		},
+		{
+			name: "line after inline code starts flush",
+			md:   "Run `hey box list`\nthen choose a box",
+			want: "<p>Run <code>hey box list</code><br>then choose a box</p>",
+		},
+		{
+			name: "line after image starts flush",
+			md:   "![Revenue chart](https://example.com/chart.png)\nReview the chart",
+			want: `<p><img src="https://example.com/chart.png" alt="Revenue chart"><br>Review the chart</p>`,
+		},
+		{
+			name: "wrapped list item keeps its structure",
+			md:   "- First line\n  second line",
+			want: "<ul>\n<li>First line<br>second line</li>\n</ul>",
+		},
+		{
+			name: "wrapped blockquote keeps its structure",
+			md:   "> First line\n> second line",
+			want: "<blockquote>\n<p>First line<br>second line</p>\n</blockquote>",
+		},
 		{
 			name: "inline emphasis and strikethrough",
 			md:   "**bold** and *italic* and ~~gone~~",
@@ -53,11 +93,21 @@ func TestFromMarkdown(t *testing.T) {
 			md:   "<div>raw <strong>html</strong></div>",
 			want: "<div>raw <strong>html</strong></div>",
 		},
+		{
+			name: "raw preformatted HTML keeps break-adjacent whitespace",
+			md:   "<pre>first<br>\n second</pre>",
+			want: "<pre>first<br>\n second</pre>",
+		},
 		{
 			name: "code span and fence stay verbatim",
 			md:   "`hey box list`\n\n```\nmake test\n```",
 			want: "<p><code>hey box list</code></p>\n<pre><code>make test\n</code></pre>",
 		},
+		{
+			name: "fenced code preserves newlines and literal breaks",
+			md:   "```\nfirst<br>\n second\n```",
+			want: "<pre><code>first&lt;br&gt;\n second\n</code></pre>",
+		},
 		{
 			name: "fence language becomes HEY's pre attribute",
 			md:   "```ruby\nputs \"hey\"\n```",
@@ -94,6 +144,22 @@ func TestFromMarkdown(t *testing.T) {
 	}
 }
 
+func TestMarkdownHardBreakRoundTripKeepsItsMeaningWithoutHTMLWhitespace(t *testing.T) {
+	const source = "AAA.\nBBB.\n\nCCC."
+	const body = "<p>AAA.<br>BBB.</p>\n<p>CCC.</p>"
+
+	if got := FromMarkdown(source); got != body {
+		t.Fatalf("FromMarkdown() = %q, want %q", got, body)
+	}
+	markdown := ToMarkdown(body).String()
+	if want := "AAA.  \nBBB.\n\nCCC."; markdown != want {
+		t.Fatalf("ToMarkdown() = %q, want %q", markdown, want)
+	}
+	if got := FromMarkdown(markdown); got != body {
+		t.Errorf("FromMarkdown(ToMarkdown()) = %q, want %q", got, body)
+	}
+}
+
 func TestPrependHTML(t *testing.T) {
 	got := PrependHTML("<div>Forwarded message</div>", "<p>For <strong>your</strong> review</p>")
 	want := "<p>For <strong>your</strong> review</p><br><div>Forwarded message</div>"
diff --git a/internal/tui/compose_test.go b/internal/tui/compose_test.go
index 74840cd8..7b07bf09 100644
--- a/internal/tui/compose_test.go
+++ b/internal/tui/compose_test.go
@@ -513,7 +513,7 @@ func TestComposeBodyIsMarkdown(t *testing.T) {
 	f.body.SetValue("**Bold** move\nsee the list:\n\n- budget\n- hiring")
 
 	_, _, _, _, body := f.values()
-	want := "<p><strong>Bold</strong> move<br>\nsee the list:</p>\n<ul>\n<li>budget</li>\n<li>hiring</li>\n</ul>"
+	want := "<p><strong>Bold</strong> move<br>see the list:</p>\n<ul>\n<li>budget</li>\n<li>hiring</li>\n</ul>"
 	if body != want {
 		t.Errorf("body = %q, want %q", body, want)
 	}