diff --git a/apps/desktop/src/lib/markdown-code.test.ts b/apps/desktop/src/lib/markdown-code.test.ts
index f71f564c1c2ab..79c5d091beb3c 100644
--- a/apps/desktop/src/lib/markdown-code.test.ts
+++ b/apps/desktop/src/lib/markdown-code.test.ts
@@ -1,6 +1,6 @@
 import { describe, expect, it } from 'vitest'
 
-import { isLikelyProseCodeBlock } from './markdown-code'
+import { isLikelyProseCodeBlock, isLikelyProseFence, isLikelyStructuredText } from './markdown-code'
 
 describe('isLikelyProseCodeBlock', () => {
   it('detects prose that Streamdown mislabels as an unknown language', () => {
@@ -20,4 +20,78 @@ describe('isLikelyProseCodeBlock', () => {
   it('keeps real code blocks', () => {
     expect(isLikelyProseCodeBlock('ts', 'const value = { bunny: true };\nreturn value')).toBe(false)
   })
+
+  it('keeps an SSH config block fenced (regression: rendered as flat prose)', () => {
+    const ssh = ['Host 192.168.0.159', '    HostName 192.168.0.159', '    User teknium', '    Port 22'].join('\n')
+
+    expect(isLikelyProseCodeBlock('', ssh)).toBe(false)
+    expect(isLikelyProseCodeBlock('text', ssh)).toBe(false)
+  })
+
+  it('keeps a flat key-value config fenced', () => {
+    expect(isLikelyProseCodeBlock('', ['Host myserver', 'User teknium', 'Port 22'].join('\n'))).toBe(false)
+  })
+
+  it('keeps an .env-style dump fenced', () => {
+    expect(isLikelyProseCodeBlock('', ['API_KEY=abc123', 'PORT=8080', 'DEBUG=true'].join('\n'))).toBe(false)
+  })
+})
+
+describe('isLikelyStructuredText', () => {
+  it('flags indented config stanzas', () => {
+    expect(
+      isLikelyStructuredText(['Host x', '    HostName 10.0.0.1', '    Port 22'].join('\n'))
+    ).toBe(true)
+  })
+
+  it('flags flat key-value / settings listings', () => {
+    expect(isLikelyStructuredText(['Host myserver', 'User teknium', 'Port 22'].join('\n'))).toBe(true)
+    expect(isLikelyStructuredText(['API_KEY=abc123', 'PORT=8080', 'DEBUG=true'].join('\n'))).toBe(true)
+  })
+
+  it('does NOT flag real wrapped prose', () => {
+    expect(
+      isLikelyStructuredText(
+        [
+          'This is the first sentence of a paragraph.',
+          'Here is a second line that continues the thought.',
+          'And a third concluding line follows here.'
+        ].join('\n')
+      )
+    ).toBe(false)
+  })
+
+  it('does NOT flag prose without a config shape', () => {
+    expect(
+      isLikelyStructuredText(
+        ['the quick brown fox jumps', 'over the lazy sleeping dog', 'while the sun sets slowly'].join('\n')
+      )
+    ).toBe(false)
+  })
+
+  it('ignores single-line blocks', () => {
+    expect(isLikelyStructuredText('Port 22')).toBe(false)
+  })
+})
+
+describe('isLikelyProseFence', () => {
+  it('keeps an SSH config block fenced', () => {
+    const ssh = ['Host 192.168.0.159', '    HostName 192.168.0.159', '    User teknium', '    Port 22'].join('\n')
+
+    expect(isLikelyProseFence('', ssh)).toBe(false)
+    expect(isLikelyProseFence('text', ssh)).toBe(false)
+  })
+
+  it('still unwraps a plain-language paragraph fence', () => {
+    expect(
+      isLikelyProseFence(
+        '',
+        [
+          'This is the first sentence of a paragraph.',
+          'Here is a second line that continues the thought.',
+          'And a third concluding line follows here.'
+        ].join('\n')
+      )
+    ).toBe(true)
+  })
 })
diff --git a/apps/desktop/src/lib/markdown-code.ts b/apps/desktop/src/lib/markdown-code.ts
index 4b1632b986034..ccad28422873d 100644
--- a/apps/desktop/src/lib/markdown-code.ts
+++ b/apps/desktop/src/lib/markdown-code.ts
@@ -273,6 +273,69 @@ function codeSignals(body: string): CodeSignals {
   }
 }
 
+// A sentence-ending punctuation mark followed by whitespace or end-of-line.
+// Real wrapped prose has these; config/structured listings almost never do.
+const SENTENCE_PUNCTUATION_RE = /[.!?](?:\s|$)/
+// `Key: value` / `Key = value` — a settings/directive line with an explicit
+// separator. Unambiguous config shape.
+const CONFIG_SEPARATOR_LINE_RE = /^[A-Za-z0-9_][\w.-]*\s*[:=]\s*\S/
+// A bare identifier that could be a config key (`Host`, `Port`, `HostName`,
+// `API_KEY`). Used only for the short `Key value` directive form below.
+const CONFIG_KEY_RE = /^[A-Za-z0-9_][\w.-]*$/
+
+// True when a single line looks like a config directive rather than prose.
+// Either an explicit `Key: value` / `Key = value`, or a short whitespace
+// directive of 2-3 tokens led by an identifier (`Host example`, `Port 22`,
+// `HostName 10.0.0.1`). The token cap is what separates it from prose — a
+// real sentence line has more words than a config directive, so a
+// punctuation-less prose fragment like `the quick brown fox jumps` (5 tokens)
+// is NOT treated as config.
+function isConfigDirectiveLine(line: string): boolean {
+  const trimmed = line.trim()
+
+  if (CONFIG_SEPARATOR_LINE_RE.test(trimmed)) {
+    return true
+  }
+
+  const tokens = trimmed.split(/\s+/)
+
+  return tokens.length >= 2 && tokens.length <= 3 && CONFIG_KEY_RE.test(tokens[0])
+}
+
+/**
+ * True when a fenced block looks like structured / config / tabular text
+ * rather than wrapped prose. Such blocks (SSH config, .env dumps, INI-style
+ * settings, key/value listings) trip the prose heuristics' "3+ plain lines,
+ * no JS/SQL tokens" rule and get their fence stripped — rendering as a flat
+ * paragraph instead of a code block. This veto keeps them fenced.
+ *
+ * Two signals, biased toward keeping the fence when ambiguous:
+ *   - ANY indented continuation line (leading whitespace before content):
+ *     prose is not indented line-by-line, but config stanzas are
+ *     (`Host x` / `    HostName y`).
+ *   - No sentence-ending punctuation AND a majority of lines are
+ *     `Key value` / `Key: value` directives (see isConfigDirectiveLine).
+ */
+export function isLikelyStructuredText(body: string): boolean {
+  const lines = body.split('\n').filter(line => line.trim())
+
+  if (lines.length < 2) {
+    return false
+  }
+
+  if (lines.some(line => /^\s+\S/.test(line))) {
+    return true
+  }
+
+  if (lines.some(line => SENTENCE_PUNCTUATION_RE.test(line.trim()))) {
+    return false
+  }
+
+  const configLines = lines.filter(line => isConfigDirectiveLine(line)).length
+
+  return configLines >= Math.max(2, Math.ceil(lines.length * 0.6))
+}
+
 export function isLikelyProseFence(info: string, body: string): boolean {
   const trimmedInfo = info.trim()
   const rawInfo = trimmedInfo.toLowerCase()
@@ -302,6 +365,13 @@ export function isLikelyProseFence(info: string, body: string): boolean {
     return false
   }
 
+  // Config / key-value / indented listings are not prose — keep their fence
+  // so an SSH config, .env, or INI block renders as a code block instead of
+  // being unwrapped into a paragraph.
+  if (isLikelyStructuredText(body)) {
+    return false
+  }
+
   return (
     (signals.bulletLines >= 2 && signals.hasMarkdown && signals.codeSignals <= 2) ||
     (signals.proseLines >= 3 && signals.codeSignals === 0)
@@ -316,10 +386,19 @@ export function isLikelyProseCodeBlock(language: string | undefined, code: strin
     return false
   }
 
+  // A bullet list with markdown emphasis is prose even when it happens to be
+  // structured; the config veto below is only meant to protect config/kv
+  // listings, so let the bullet-prose case win first.
   if (signals.bulletLines >= 1 && (signals.hasMarkdown || signals.proseLines >= 2)) {
     return true
   }
 
+  // Config / key-value / indented listings are code, not prose — never
+  // unwrap them (SSH config, .env, INI, key/value tables).
+  if (isLikelyStructuredText(code || '')) {
+    return false
+  }
+
   if (NON_CODE_FENCE_LANGUAGES.has(cleanLanguage)) {
     return signals.proseLines >= 3 && signals.codeSignals === 0
   }