diff --git a/open-sse/mcp-server/descriptionCompressor.ts b/open-sse/mcp-server/descriptionCompressor.ts
index e69a86ee4d..de08898e25 100644
--- a/open-sse/mcp-server/descriptionCompressor.ts
+++ b/open-sse/mcp-server/descriptionCompressor.ts
@@ -65,9 +65,9 @@ export function compressMcpDescription(description: string): DescriptionCompress
   const applied = applyRulesToText(text, rules).text;
   const normalized = applied
     .replace(/[ \t]{2,}/g, " ")
-    .replace(/[ \t]+([,.;:!?])/g, "$1")
+    .replace(/[ \t]([,.;:!?])/g, "$1")
     .replace(/\n{3,}/g, "\n\n")
-    .replace(/(^|[.!?][ \t]+|\n+[ \t]*)([a-z])/g, (_match, prefix: string, char: string) => {
+    .replace(/(^|[.!?][ \t]|\n[ \t]*)([a-z])/g, (_match, prefix: string, char: string) => {
       return `${prefix}${char.toUpperCase()}`;
     })
     .trim();
diff --git a/open-sse/services/compression/caveman.ts b/open-sse/services/compression/caveman.ts
index 476be8d41e..b6050edf26 100644
--- a/open-sse/services/compression/caveman.ts
+++ b/open-sse/services/compression/caveman.ts
@@ -205,7 +205,7 @@ export function applyRulesToText(
 function cleanupArtifacts(text: string): string {
   let result = text;
   if (result.includes("  ")) result = result.replace(/[ \t]{2,}/g, " ");
-  if (/[\t ]+[,.;:!?]/.test(result)) result = result.replace(/[ \t]+([,.;:!?])/g, "$1");
+  if (/[\t ]+[,.;:!?]/.test(result)) result = result.replace(/[ \t]([,.;:!?])/g, "$1");
   if (/[.!?]{2,}/.test(result)) result = result.replace(/([.!?]){2,}/g, "$1");
   if (/[ \t]\n/.test(result)) result = result.replace(/[ \t]+$/gm, "");
   if (result.endsWith(" ") || result.endsWith("\t")) result = result.trimEnd();
@@ -216,12 +216,9 @@ function cleanupArtifacts(text: string): string {
 }
 
 function recapitalizeSentences(text: string): string {
-  return text.replace(
-    /(^|[.!?][ \t]+|\n+[ \t]*)([a-z])/g,
-    (_match, prefix: string, char: string) => {
-      return `${prefix}${char.toUpperCase()}`;
-    }
-  );
+  return text.replace(/(^|[.!?][ \t]|\n[ \t]*)([a-z])/g, (_match, prefix: string, char: string) => {
+    return `${prefix}${char.toUpperCase()}`;
+  });
 }
 
 function createCavemanStats(
@@ -365,7 +362,7 @@ export function cavemanCompress(
       const { text: rulesApplied, appliedRules } = applyRulesToText(extractedText, rules);
       allAppliedRules.push(...appliedRules);
 
-      const normalized = cleanupArtifacts(recapitalizeSentences(rulesApplied));
+      const normalized = recapitalizeSentences(cleanupArtifacts(rulesApplied));
       const cleaned =
         blocks.length > 0
           ? cleanupArtifacts(restorePreservedBlocks(normalized, blocks))
diff --git a/open-sse/services/compression/validation.ts b/open-sse/services/compression/validation.ts
index 7f2ae31115..152b8a2221 100644
--- a/open-sse/services/compression/validation.ts
+++ b/open-sse/services/compression/validation.ts
@@ -59,7 +59,7 @@ export function validateCompression(original: string, compressed: string): Valid
   );
   requireExactPresence(
     "markdown link",
-    collectMatches(original, /\[[^\]\n]{1,1000}\]\([^)[ \t\n]{1,2000}(?:[ \t]+"[^"]{0,1000}")?\)/g),
+    collectMatches(original, /\[[^\]\n]{1,1000}\]\([^)\n]{1,2000}\)/g),
     compressed,
     errors
   );
@@ -67,7 +67,7 @@ export function validateCompression(original: string, compressed: string): Valid
   requireExactPresence("heading", collectMatches(original, /^#{1,6}\s+.+$/gm), compressed, errors);
   requireExactPresence(
     "table row",
-    collectMatches(original, /^[ \t]*\|(?:[^|\n]{0,1000}\|){1,100}[ \t]*$/gm),
+    collectMatches(original, /^[ \t]*\|(?:[^|\n]{0,1000}\|){1,100}/gm),
     compressed,
     errors
   );