diff --git a/agent/agent_test.go b/agent/agent_test.go
index e21806f845..410b0941f9 100644
--- a/agent/agent_test.go
+++ b/agent/agent_test.go
@@ -2229,12 +2229,25 @@ func TestAgent_ReconnectingPTY(t *testing.T) {
 				return strings.Contains(line, "exit") || strings.Contains(line, "logout")
 			}
 
-			// Wait for the prompt before writing commands.  If the command arrives before the prompt is written, screen
-			// will sometimes put the command output on the same line as the command and the test will flake
+			// Wait for the prompt before writing commands. If the command
+			// arrives before the prompt is written, screen will sometimes put
+			// the command output on the same line as the command and the test
+			// will flake.
 			require.NoError(t, tr1.ReadUntil(ctx, matchPrompt), "find prompt")
 			require.NoError(t, tr2.ReadUntil(ctx, matchPrompt), "find prompt")
 
 			data, err := json.Marshal(workspacesdk.ReconnectingPTYRequest{
+				Data: "printf '%s\\n' \"$TERM\"\r",
+			})
+			require.NoError(t, err)
+			_, err = netConn1.Write(data)
+			require.NoError(t, err)
+			require.NoError(t, tr1.ReadUntilString(ctx, "xterm-256color"), "find TERM output")
+			require.NoError(t, tr2.ReadUntilString(ctx, "xterm-256color"), "find TERM output")
+			require.NoError(t, tr1.ReadUntil(ctx, matchPrompt), "find prompt")
+			require.NoError(t, tr2.ReadUntil(ctx, matchPrompt), "find prompt")
+
+			data, err = json.Marshal(workspacesdk.ReconnectingPTYRequest{
 				Data: "echo test\r",
 			})
 			require.NoError(t, err)
diff --git a/agent/reconnectingpty/buffered.go b/agent/reconnectingpty/buffered.go
index 25ba1ee136..385d6ef7f7 100644
--- a/agent/reconnectingpty/buffered.go
+++ b/agent/reconnectingpty/buffered.go
@@ -60,7 +60,7 @@ func newBuffered(ctx context.Context, logger slog.Logger, execer agentexec.Exece
 	// first argument so remove it.
 	cmdWithEnv := execer.PTYCommandContext(ctx, cmd.Path, cmd.Args[1:]...)
 	//nolint:gocritic
-	cmdWithEnv.Env = append(rpty.command.Env, "TERM=xterm-256color")
+	cmdWithEnv.Env = append(rpty.command.Env, "TERM="+xterm256Color)
 	cmdWithEnv.Dir = rpty.command.Dir
 	ptty, process, err := pty.Start(cmdWithEnv)
 	if err != nil {
diff --git a/agent/reconnectingpty/reconnectingpty.go b/agent/reconnectingpty/reconnectingpty.go
index 82b018cf7b..c3fa833b41 100644
--- a/agent/reconnectingpty/reconnectingpty.go
+++ b/agent/reconnectingpty/reconnectingpty.go
@@ -19,11 +19,17 @@ import (
 	"github.com/coder/coder/v2/pty"
 )
 
-// attachTimeout is the initial timeout for attaching and will probably be far
-// shorter than the reconnect timeout in most cases; in tests it might be
-// longer.  It should be at least long enough for the first screen attach to be
-// able to start up the daemon and for the buffered pty to start.
-const attachTimeout = 30 * time.Second
+const (
+	// attachTimeout is the initial timeout for attaching and will probably be far
+	// shorter than the reconnect timeout in most cases; in tests it might be
+	// longer.  It should be at least long enough for the first screen attach to be
+	// able to start up the daemon and for the buffered pty to start.
+	attachTimeout = 30 * time.Second
+
+	// xterm256Color is the terminal type exposed to commands running in the web
+	// terminal.
+	xterm256Color = "xterm-256color"
+)
 
 // Options allows configuring the reconnecting pty.
 type Options struct {
diff --git a/agent/reconnectingpty/screen.go b/agent/reconnectingpty/screen.go
index 221713d212..a2fcb4fba2 100644
--- a/agent/reconnectingpty/screen.go
+++ b/agent/reconnectingpty/screen.go
@@ -103,6 +103,13 @@ func newScreen(ctx context.Context, logger slog.Logger, execer agentexec.Execer,
 		// output when scrolling back with the mouse wheel (copy mode still works
 		// since that is screen itself scrolling).
 		"altscreen on",
+		// Match the background color erase capability advertised by xterm-256color.
+		"defbce on",
+		// Keep the shell environment aligned with the web terminal emulator. Some
+		// terminal applications, including tmux, render differently when they see
+		// screen.xterm-256color even though screen is only an implementation
+		// detail for reconnecting.
+		"term " + xterm256Color,
 		// Remap the control key to C-s since C-a may be used in applications.  C-s
 		// is chosen because it cannot actually be used because by default it will
 		// pause and C-q to resume will just kill the browser window.  We may not
@@ -230,7 +237,7 @@ func (rpty *screenReconnectingPTY) doAttach(ctx context.Context, conn net.Conn,
 		// pty.Cmd duplicates Path as the first argument so remove it.
 	}, rpty.command.Args[1:]...)...)
 	//nolint:gocritic
-	cmd.Env = append(rpty.command.Env, "TERM=xterm-256color")
+	cmd.Env = append(rpty.command.Env, "TERM="+xterm256Color)
 	cmd.Dir = rpty.command.Dir
 	ptty, process, err := pty.Start(cmd, pty.WithPTYOption(
 		pty.WithSSHRequest(ssh.Pty{
@@ -346,7 +353,7 @@ func (rpty *screenReconnectingPTY) sendCommand(ctx context.Context, command stri
 			"-X", command,
 		)
 		//nolint:gocritic
-		cmd.Env = append(rpty.command.Env, "TERM=xterm-256color")
+		cmd.Env = append(rpty.command.Env, "TERM="+xterm256Color)
 		cmd.Dir = rpty.command.Dir
 		cmd.Stdout = &stdout
 		err := cmd.Run()
diff --git a/site/src/modules/terminal/WorkspaceTerminal.tsx b/site/src/modules/terminal/WorkspaceTerminal.tsx
index 418140c200..3cad12fd46 100644
--- a/site/src/modules/terminal/WorkspaceTerminal.tsx
+++ b/site/src/modules/terminal/WorkspaceTerminal.tsx
@@ -164,6 +164,12 @@ export const WorkspaceTerminal = ({
 		const nextTerminal = new Terminal({
 			allowProposedApi: true,
 			allowTransparency: true,
+			// Use the selected terminal font for block element, box drawing,
+			// quadrant, and powerline glyphs. xterm's custom glyph renderer helps
+			// when fonts lack powerline glyphs, but it changes block and quadrant
+			// shapes and breaks TUIs that use them for pixel art, like Claude
+			// Code's logo.
+			customGlyphs: false,
 			disableStdin: false,
 			fontFamily: terminalFontFamily,
 			fontSize: 16,
diff --git a/site/src/theme/constants.test.ts b/site/src/theme/constants.test.ts
new file mode 100644
index 0000000000..3ea061fcb4
--- /dev/null
+++ b/site/src/theme/constants.test.ts
@@ -0,0 +1,9 @@
+import { terminalFonts } from "./constants";
+
+describe("terminalFonts", () => {
+	it("uses the terminal symbol fallback before generic monospace", () => {
+		for (const fontFamily of Object.values(terminalFonts)) {
+			expect(fontFamily).toMatch(/'Coder Terminal Symbols', monospace$/);
+		}
+	});
+});
diff --git a/site/src/theme/constants.ts b/site/src/theme/constants.ts
index 62274d5001..8b54c8d1a6 100644
--- a/site/src/theme/constants.ts
+++ b/site/src/theme/constants.ts
@@ -3,30 +3,30 @@ import type { TerminalFontName } from "#/api/typesGenerated";
 export const borderRadius = 8;
 
 const MONOSPACE_DEFAULT_FONT = "Geist Mono Variable";
+const TERMINAL_SYMBOL_FONT = "'Coder Terminal Symbols'";
 export const MONOSPACE_FONT_FAMILY =
 	"'Geist Mono Variable', 'IBM Plex Mono', 'Lucida Console', 'Lucida Sans Typewriter', 'Liberation Mono', 'Monaco', 'Courier New', Courier, monospace";
 export const BODY_FONT_FAMILY = `"Geist Variable", system-ui, sans-serif`;
 
-export const terminalFonts: Record<TerminalFontName, string> = {
-	"fira-code": MONOSPACE_FONT_FAMILY.replace(
-		MONOSPACE_DEFAULT_FONT,
-		"Fira Code",
-	),
-	"jetbrains-mono": MONOSPACE_FONT_FAMILY.replace(
-		MONOSPACE_DEFAULT_FONT,
-		"JetBrains Mono",
-	),
-	"source-code-pro": MONOSPACE_FONT_FAMILY.replace(
-		MONOSPACE_DEFAULT_FONT,
-		"Source Code Pro",
-	),
-	"ibm-plex-mono": MONOSPACE_FONT_FAMILY.replace(
-		MONOSPACE_DEFAULT_FONT,
-		"IBM Plex Mono",
-	),
-	"geist-mono": MONOSPACE_FONT_FAMILY,
+const withTerminalSymbolFallback = (fontFamily: string) =>
+	fontFamily.replace(", monospace", `, ${TERMINAL_SYMBOL_FONT}, monospace`);
 
-	"": MONOSPACE_FONT_FAMILY,
+export const terminalFonts: Record<TerminalFontName, string> = {
+	"fira-code": withTerminalSymbolFallback(
+		MONOSPACE_FONT_FAMILY.replace(MONOSPACE_DEFAULT_FONT, "Fira Code"),
+	),
+	"jetbrains-mono": withTerminalSymbolFallback(
+		MONOSPACE_FONT_FAMILY.replace(MONOSPACE_DEFAULT_FONT, "JetBrains Mono"),
+	),
+	"source-code-pro": withTerminalSymbolFallback(
+		MONOSPACE_FONT_FAMILY.replace(MONOSPACE_DEFAULT_FONT, "Source Code Pro"),
+	),
+	"ibm-plex-mono": withTerminalSymbolFallback(
+		MONOSPACE_FONT_FAMILY.replace(MONOSPACE_DEFAULT_FONT, "IBM Plex Mono"),
+	),
+	"geist-mono": withTerminalSymbolFallback(MONOSPACE_FONT_FAMILY),
+
+	"": withTerminalSymbolFallback(MONOSPACE_FONT_FAMILY),
 };
 export const terminalFontLabels: Record<TerminalFontName, string> = {
 	"geist-mono": "Geist Mono",
diff --git a/site/src/theme/fonts/coder-terminal-symbols-LICENSE.txt b/site/src/theme/fonts/coder-terminal-symbols-LICENSE.txt
new file mode 100644
index 0000000000..06eb073d6b
--- /dev/null
+++ b/site/src/theme/fonts/coder-terminal-symbols-LICENSE.txt
@@ -0,0 +1,21 @@
+The MIT License (MIT)
+
+Copyright (c) 2014 Ryan L McIntyre
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.
diff --git a/site/src/theme/fonts/coder-terminal-symbols-powerline.woff2 b/site/src/theme/fonts/coder-terminal-symbols-powerline.woff2
new file mode 100644
index 0000000000..37471be442
Binary files /dev/null and b/site/src/theme/fonts/coder-terminal-symbols-powerline.woff2 differ
diff --git a/site/src/theme/fonts/coder-terminal-symbols.css b/site/src/theme/fonts/coder-terminal-symbols.css
new file mode 100644
index 0000000000..2bbf395694
--- /dev/null
+++ b/site/src/theme/fonts/coder-terminal-symbols.css
@@ -0,0 +1,12 @@
+/*
+ * Powerline fallback glyphs subset from Symbols Nerd Font Mono v3.4.0.
+ * Source: https://github.com/ryanoasis/nerd-fonts/releases/tag/v3.4.0
+ */
+@font-face {
+	font-family: "Coder Terminal Symbols";
+	font-style: normal;
+	font-display: swap;
+	font-weight: 400 700;
+	src: url("./coder-terminal-symbols-powerline.woff2?no-inline") format("woff2");
+	unicode-range: U+E0A0, U+E0B0-E0BF;
+}
diff --git a/site/src/theme/globalFonts.ts b/site/src/theme/globalFonts.ts
index aab84ed7c2..2edf8cc550 100644
--- a/site/src/theme/globalFonts.ts
+++ b/site/src/theme/globalFonts.ts
@@ -5,6 +5,7 @@ import "@fontsource/ibm-plex-mono/600.css";
 import "@fontsource-variable/geist";
 import "@fontsource-variable/geist-mono";
 // Alternative fonts for Terminal
+import "./fonts/coder-terminal-symbols.css";
 import "@fontsource/fira-code/400.css";
 import "@fontsource/fira-code/600.css";
 import "@fontsource/source-code-pro/400.css";