diff --git a/src/pages/admin/bots/[bot_id]/(data)/message-markdown-components.tsx b/src/pages/admin/bots/[bot_id]/(data)/message-markdown-components.tsx
index e94217d..a9b94c7 100644
--- a/src/pages/admin/bots/[bot_id]/(data)/message-markdown-components.tsx
+++ b/src/pages/admin/bots/[bot_id]/(data)/message-markdown-components.tsx
@@ -42,7 +42,7 @@ export const MessageMarkdownComponents: Components = {
         </MarkdownList>
     ),
     code: ({ children }) => (
-        <Span className="font-mono text-[13px] px-1 py-px rounded-default-xs bg-sunken text-ink break-words">
+        <Span className="font-mono text-[13px] px-1 py-px rounded-default-xs bg-sunken text-ink wrap-anywhere">
             {children}
         </Span>
     ),
@@ -58,7 +58,7 @@ export const MessageMarkdownComponents: Components = {
     ),
     table: ({ children }) => (
         <Stack className="w-full max-w-full overflow-x-auto items-start">
-            <table className="text-[13px] leading-5 text-ink border-collapse">{children}</table>
+            <table className="text-[13px] leading-5 text-ink border-collapse wrap-break-word">{children}</table>
         </Stack>
     ),
     th: ({ children }) => (
diff --git a/src/pages/admin/bots/[bot_id]/(data)/user-markdown-components.tsx b/src/pages/admin/bots/[bot_id]/(data)/user-markdown-components.tsx
index 365ac65..7085a55 100644
--- a/src/pages/admin/bots/[bot_id]/(data)/user-markdown-components.tsx
+++ b/src/pages/admin/bots/[bot_id]/(data)/user-markdown-components.tsx
@@ -39,7 +39,7 @@ export const UserMarkdownComponents: Components = {
         </MarkdownList>
     ),
     code: ({ children }) => (
-        <Span className="font-mono text-[13px] px-1 py-px rounded-default-xs bg-on-ink/15 text-on-ink break-words">
+        <Span className="font-mono text-[13px] px-1 py-px rounded-default-xs bg-on-ink/15 text-on-ink wrap-anywhere">
             {children}
         </Span>
     ),
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/bot-message-line.tsx b/src/pages/admin/bots/[bot_id]/(partials)/bot-message-line.tsx
index 77665e2..f536eb1 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/bot-message-line.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/bot-message-line.tsx
@@ -65,7 +65,7 @@ function BotMessageLine({ message, bot_name, at }: Props) {
             ) : null}
             <Stack
                 {...{ [QuotableAttribute]: "" }}
-                className="w-full gap-2.5! items-start break-words"
+                className="w-full gap-2.5! items-start wrap-anywhere [&>*]:max-w-full"
             >
                 <Markdown
                     remarkPlugins={RemarkPlugins}
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/bot-ref-chip.tsx b/src/pages/admin/bots/[bot_id]/(partials)/bot-ref-chip.tsx
index 8df8b32..0e16c4f 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/bot-ref-chip.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/bot-ref-chip.tsx
@@ -35,7 +35,7 @@ export default function BotRefChip({ bot_id }: Props) {
                     : `/admin/bots/${bot.id}`
             }
             title={`Open ${bot.name}`}
-            className="inline-flex h-6 gap-1.5 items-center px-1.5 align-middle rounded-default-xs border-0 bg-sunken text-[13px] font-bold leading-4 text-ink whitespace-nowrap hover:opacity-80"
+            className="inline-flex h-6 max-w-full gap-1.5 items-center px-1.5 align-middle rounded-default-xs border-0 bg-sunken text-[13px] font-bold leading-4 text-ink whitespace-nowrap hover:opacity-80"
         >
             <BotAvatar
                 image_media_id={bot.image_media_id}
@@ -43,9 +43,10 @@ export default function BotRefChip({ bot_id }: Props) {
                 face={(bot.face || "idle") as BotFace}
                 label={bot.name || ""}
                 size={18}
+                className="shrink-0"
             />
-            {bot.name}
-            {workspace_id && bot.is_admin ? <AdminShield size={13} /> : null}
+            <Span className="min-w-0 truncate">{bot.name}</Span>
+            {workspace_id && bot.is_admin ? <AdminShield size={13} className="shrink-0" /> : null}
         </Link>
     );
 }
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/computer-ref-chip.tsx b/src/pages/admin/bots/[bot_id]/(partials)/computer-ref-chip.tsx
index 81fc1f0..24b4767 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/computer-ref-chip.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/computer-ref-chip.tsx
@@ -38,14 +38,15 @@ export default function ComputerRefChip({ computer_id }: Props) {
                 openComputer({ computer_id: computer.id || 0, mode: "browser" })
             }
             className={twMerge(
-                "inline-flex h-6 gap-1.5! flex-nowrap align-middle px-2! text-[13px] font-bold whitespace-nowrap text-ink dark:text-ink",
+                "inline-flex h-6 max-w-full gap-1.5! flex-nowrap align-middle px-2! text-[13px] font-bold whitespace-nowrap text-ink dark:text-ink",
+                "[&_.twui-button-content-wrapper]:min-w-0",
                 current
                     ? "bg-sunken hover:bg-sunken outline-0"
                     : "bg-transparent hover:bg-sunken",
             )}
         >
             <Monitor size={14} aria-hidden className="shrink-0" />
-            {name}
+            <Span className="min-w-0 truncate">{name}</Span>
             {current ? <Check size={14} aria-hidden className="shrink-0" /> : null}
         </Button>
     );
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/crew-message-line.tsx b/src/pages/admin/bots/[bot_id]/(partials)/crew-message-line.tsx
index f17ed17..dd97395 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/crew-message-line.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/crew-message-line.tsx
@@ -22,7 +22,7 @@ type Props = {
  */
 function CrewMessageLine({ message }: Props) {
     return (
-        <Stack className="w-full gap-2.5! items-start break-words">
+        <Stack className="w-full gap-2.5! items-start wrap-anywhere [&>*]:max-w-full">
             <Markdown remarkPlugins={RemarkPlugins} components={MessageMarkdownComponents}>
                 {linkComputerRefs({ text: message.text || "" })}
             </Markdown>
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/hook-proposal-ref-chip.tsx b/src/pages/admin/bots/[bot_id]/(partials)/hook-proposal-ref-chip.tsx
index af11127..d976b34 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/hook-proposal-ref-chip.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/hook-proposal-ref-chip.tsx
@@ -1,4 +1,5 @@
 import { useState } from "react";
+import { twMerge } from "tailwind-merge";
 import Modal from "@moduletrace/twui/elements/Modal";
 import Button from "@moduletrace/twui/layout/Button";
 import H2 from "@moduletrace/twui/layout/H2";
@@ -43,13 +44,16 @@ export default function HookProposalRefChip({ proposal_id }: Props) {
                     color="gray"
                     size="smaller"
                     title={`Review: ${title}`}
-                    className="inline-flex h-6 gap-1.5! flex-nowrap align-middle px-2! text-[13px] font-bold text-ink whitespace-nowrap"
+                    className={twMerge(
+                        "inline-flex h-6 max-w-full gap-1.5! flex-nowrap align-middle px-2! text-[13px] font-bold text-ink whitespace-nowrap",
+                        "[&_.twui-button-content-wrapper]:min-w-0",
+                    )}
                 >
                     <Webhook size={14} aria-hidden className="shrink-0" />
-                    {`${title} · ${status}`}
+                    <Span className="min-w-0 truncate">{`${title} · ${status}`}</Span>
                 </Button>
             }
-            targetWrapperProps={{ className: "inline-flex align-middle" }}
+            targetWrapperProps={{ className: "inline-flex max-w-full align-middle" }}
             open={open}
             setOpen={setOpen}
             className="max-w-xl bg-paper p-6"
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/markdown-link.tsx b/src/pages/admin/bots/[bot_id]/(partials)/markdown-link.tsx
index 018bdd1..379dd4d 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/markdown-link.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/markdown-link.tsx
@@ -121,7 +121,7 @@ export default function MarkdownLink({ href, children }: ComponentProps<"a">) {
             href={href}
             target="_blank"
             rel="noopener noreferrer"
-            className="text-ink underline underline-offset-2 hover:opacity-80 break-words"
+            className="text-ink underline underline-offset-2 hover:opacity-80 wrap-anywhere"
         >
             {children}
         </Link>
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/markdown-list.tsx b/src/pages/admin/bots/[bot_id]/(partials)/markdown-list.tsx
index c026acb..fba60a1 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/markdown-list.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/markdown-list.tsx
@@ -26,7 +26,7 @@ export default function MarkdownList({ children, ordered, start, className }: Pr
             start={start}
             items={items}
             className={twMerge(
-                `w-full gap-1! pl-5 my-0 text-sm leading-5 text-ink ${ordered ? "list-decimal" : "list-disc"}`,
+                `self-stretch gap-1! pl-5 my-0 text-sm leading-5 text-ink [&>li]:max-w-full ${ordered ? "list-decimal" : "list-disc"}`,
                 className,
             )}
         />
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/proposal-ref-chip.tsx b/src/pages/admin/bots/[bot_id]/(partials)/proposal-ref-chip.tsx
index de37b5b..362bee4 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/proposal-ref-chip.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/proposal-ref-chip.tsx
@@ -1,4 +1,5 @@
 import { useState } from "react";
+import { twMerge } from "tailwind-merge";
 import Modal from "@moduletrace/twui/elements/Modal";
 import Button from "@moduletrace/twui/layout/Button";
 import H2 from "@moduletrace/twui/layout/H2";
@@ -47,13 +48,16 @@ export default function ProposalRefChip({ proposal_id }: Props) {
                     color="gray"
                     size="smaller"
                     title={`Review: ${title}`}
-                    className="inline-flex h-6 gap-1.5! flex-nowrap align-middle px-2! text-[13px] font-bold text-ink whitespace-nowrap"
+                    className={twMerge(
+                        "inline-flex h-6 max-w-full gap-1.5! flex-nowrap align-middle px-2! text-[13px] font-bold text-ink whitespace-nowrap",
+                        "[&_.twui-button-content-wrapper]:min-w-0",
+                    )}
                 >
                     <Icon size={14} aria-hidden className="shrink-0" />
-                    {`${title} · ${status}`}
+                    <Span className="min-w-0 truncate">{`${title} · ${status}`}</Span>
                 </Button>
             }
-            targetWrapperProps={{ className: "inline-flex align-middle" }}
+            targetWrapperProps={{ className: "inline-flex max-w-full align-middle" }}
             open={open}
             setOpen={setOpen}
             className="max-w-xl bg-paper p-6"
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/secret-request-ref-chip.tsx b/src/pages/admin/bots/[bot_id]/(partials)/secret-request-ref-chip.tsx
index 88341c5..de34dcc 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/secret-request-ref-chip.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/secret-request-ref-chip.tsx
@@ -1,4 +1,5 @@
 import { useState } from "react";
+import { twMerge } from "tailwind-merge";
 import Modal from "@moduletrace/twui/elements/Modal";
 import Button from "@moduletrace/twui/layout/Button";
 import H2 from "@moduletrace/twui/layout/H2";
@@ -46,13 +47,16 @@ export default function SecretRequestRefChip({ request_id }: Props) {
                     color="gray"
                     size="smaller"
                     title={view.status == "pending" ? `Enter ${view.key}` : `${view.key}: ${status}`}
-                    className="inline-flex h-6 gap-1.5! flex-nowrap align-middle px-2! text-[13px] font-bold text-ink whitespace-nowrap"
+                    className={twMerge(
+                        "inline-flex h-6 max-w-full gap-1.5! flex-nowrap align-middle px-2! text-[13px] font-bold text-ink whitespace-nowrap",
+                        "[&_.twui-button-content-wrapper]:min-w-0",
+                    )}
                 >
                     <KeyRound size={14} aria-hidden className="shrink-0" />
-                    {`${view.key} · ${status}`}
+                    <Span className="min-w-0 truncate">{`${view.key} · ${status}`}</Span>
                 </Button>
             }
-            targetWrapperProps={{ className: "inline-flex align-middle" }}
+            targetWrapperProps={{ className: "inline-flex max-w-full align-middle" }}
             open={open}
             setOpen={setOpen}
             className="max-w-xl bg-paper p-6"
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/take-over-chip.tsx b/src/pages/admin/bots/[bot_id]/(partials)/take-over-chip.tsx
index 2c237db..bf29ab5 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/take-over-chip.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/take-over-chip.tsx
@@ -1,4 +1,5 @@
 import { useContext } from "react";
+import { twMerge } from "tailwind-merge";
 import Button from "@moduletrace/twui/layout/Button";
 import Span from "@moduletrace/twui/layout/Span";
 import { Hand } from "lucide-react";
@@ -34,10 +35,13 @@ export default function TakeOverChip({ computer_id, mode }: Props) {
             size="smaller"
             title={`Open ${name} (${mode_title}) and take over`}
             onClick={() => openComputer({ computer_id, mode, take_over: true })}
-            className="inline-flex h-6 gap-1.5! flex-nowrap align-middle px-2! text-[13px] font-bold text-ink whitespace-nowrap"
+            className={twMerge(
+                "inline-flex h-6 max-w-full gap-1.5! flex-nowrap align-middle px-2! text-[13px] font-bold text-ink whitespace-nowrap",
+                "[&_.twui-button-content-wrapper]:min-w-0",
+            )}
         >
             <Hand size={14} aria-hidden className="shrink-0" />
-            {`Take over ${name} · ${mode_title}`}
+            <Span className="min-w-0 truncate">{`Take over ${name} · ${mode_title}`}</Span>
         </Button>
     );
 }
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/user-bubble.tsx b/src/pages/admin/bots/[bot_id]/(partials)/user-bubble.tsx
index b44e48b..22215cb 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/user-bubble.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/user-bubble.tsx
@@ -25,7 +25,7 @@ export default function UserBubble({ text }: { text: string }) {
             {...{ [QuotableAttribute]: "" }}
             className={twMerge(
                 "max-w-[80%] min-w-0 gap-2.5! items-stretch rounded-default-lg",
-                "bg-ink text-on-ink px-4 py-3 text-sm leading-5 break-words",
+                "bg-ink text-on-ink px-4 py-3 text-sm leading-5 wrap-anywhere",
                 "conversation-user-bubble",
             )}
         >
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/user-markdown-link.tsx b/src/pages/admin/bots/[bot_id]/(partials)/user-markdown-link.tsx
index 8e863f0..a6134bf 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/user-markdown-link.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/user-markdown-link.tsx
@@ -14,7 +14,7 @@ export default function UserMarkdownLink(props: ComponentProps<"a">) {
             href={props.href}
             target="_blank"
             rel="noopener noreferrer"
-            className="text-blue-400 dark:text-blue-600 underline underline-offset-2 hover:opacity-80 break-words"
+            className="text-blue-400 dark:text-blue-600 underline underline-offset-2 hover:opacity-80 wrap-anywhere"
         >
             {props.children}
         </Link>
diff --git a/src/pages/admin/bots/[bot_id]/(partials)/workspace-ref-chip.tsx b/src/pages/admin/bots/[bot_id]/(partials)/workspace-ref-chip.tsx
index ed001d8..59862b2 100644
--- a/src/pages/admin/bots/[bot_id]/(partials)/workspace-ref-chip.tsx
+++ b/src/pages/admin/bots/[bot_id]/(partials)/workspace-ref-chip.tsx
@@ -24,10 +24,10 @@ export default function WorkspaceRefChip({ workspace_id }: Props) {
         <Link
             href={`/admin/workspaces/${workspace.id}`}
             title={`Open ${workspace.name}`}
-            className="inline-flex h-6 gap-1.5 items-center px-1.5 align-middle rounded-default-xs border-0 bg-sunken text-[13px] font-bold leading-4 text-ink whitespace-nowrap hover:opacity-80"
+            className="inline-flex h-6 max-w-full gap-1.5 items-center px-1.5 align-middle rounded-default-xs border-0 bg-sunken text-[13px] font-bold leading-4 text-ink whitespace-nowrap hover:opacity-80"
         >
             <WorkspaceAvatar image_media_id={workspace.image_media_id} size="xs" />
-            {workspace.name}
+            <Span className="min-w-0 truncate">{workspace.name}</Span>
         </Link>
     );
 }