diff --git a/src/Cargo.lock b/src/Cargo.lock
index e748321a..833ce649 100644
--- a/src/Cargo.lock
+++ b/src/Cargo.lock
@@ -9,6 +9,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "5a15f179cd60c4584b8a8c596927aadc462e27f2ca70c04e0071964a73ba7a75"
 dependencies = [
  "cfg-if",
+ "const-random",
  "getrandom 0.3.4",
  "once_cell",
  "serde",
@@ -323,6 +324,26 @@ dependencies = [
  "memchr",
 ]
 
+[[package]]
+name = "const-random"
+version = "0.1.18"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "87e00182fe74b066627d63b85fd550ac2998d4b0bd86bfed477a0ae4c7c71359"
+dependencies = [
+ "const-random-macro",
+]
+
+[[package]]
+name = "const-random-macro"
+version = "0.1.16"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f9d839f2a20b0aee515dc581a6172f2321f96cab76c1a38a4c584a194955390e"
+dependencies = [
+ "getrandom 0.2.17",
+ "once_cell",
+ "tiny-keccak",
+]
+
 [[package]]
 name = "core-foundation"
 version = "0.10.1"
@@ -629,16 +650,6 @@ version = "1.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "42703706b716c37f96a77aea830392ad231f44c9e9a67872fa5548707e11b11c"
 
-[[package]]
-name = "futf"
-version = "0.1.5"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "df420e2e84819663797d1ec6544b13c5be84629e7bb00dc960d6917db2987843"
-dependencies = [
- "mac",
- "new_debug_unreachable",
-]
-
 [[package]]
 name = "futures"
 version = "0.3.32"
@@ -872,16 +883,16 @@ dependencies = [
 
 [[package]]
 name = "html-to-markdown-rs"
-version = "2.23.1"
+version = "2.27.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e1f4d6781ac8dd203853803d27054ca4153c7fd0f3956cb7fc95dc06f42a1c46"
+checksum = "06f53f29c48f234830ccc312f652770723419fe9b3529fa5e0b027a0fedb7869"
 dependencies = [
+ "ahash",
  "astral-tl",
  "base64",
  "html-escape",
  "html5ever",
  "lru",
- "markup5ever_rcdom",
  "once_cell",
  "regex",
  "serde",
@@ -891,9 +902,9 @@ dependencies = [
 
 [[package]]
 name = "html5ever"
-version = "0.36.1"
+version = "0.38.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6452c4751a24e1b99c3260d505eaeee76a050573e61f30ac2c924ddc7236f01e"
+checksum = "1054432bae2f14e0061e33d23402fbaa67a921d319d56adc6bcf887ddad1cbc2"
 dependencies = [
  "log",
  "markup5ever",
@@ -1382,35 +1393,17 @@ version = "0.1.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "112b39cec0b298b6c1999fee3e31427f74f676e4cb9879ed1a121b43661a4154"
 
-[[package]]
-name = "mac"
-version = "0.1.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c41e0c4fef86961ac6d6f8a82609f55f31b05e4fce149ac5710e439df7619ba4"
-
 [[package]]
 name = "markup5ever"
-version = "0.36.1"
+version = "0.38.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6c3294c4d74d0742910f8c7b466f44dda9eb2d5742c1e430138df290a1e8451c"
+checksum = "8983d30f2915feeaaab2d6babdd6bc7e9ed1a00b66b5e6d74df19aa9c0e91862"
 dependencies = [
  "log",
  "tendril",
  "web_atoms",
 ]
 
-[[package]]
-name = "markup5ever_rcdom"
-version = "0.36.0+unofficial"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3e5fc8802e8797c0dfdd2ce5c21aa0aee21abbc7b3b18559100651b3352a7b63"
-dependencies = [
- "html5ever",
- "markup5ever",
- "tendril",
- "xml5ever",
-]
-
 [[package]]
 name = "maybe-async"
 version = "0.2.10"
@@ -2594,12 +2587,11 @@ dependencies = [
 
 [[package]]
 name = "tendril"
-version = "0.4.3"
+version = "0.5.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d24a120c5fc464a3458240ee02c299ebcb9d67b5249c8848b09d639dca8d7bb0"
+checksum = "c4790fc369d5a530f4b544b094e31388b9b3a37c0f4652ade4505945f5660d24"
 dependencies = [
- "futf",
- "mac",
+ "new_debug_unreachable",
  "utf-8",
 ]
 
@@ -2643,6 +2635,15 @@ dependencies = [
  "syn",
 ]
 
+[[package]]
+name = "tiny-keccak"
+version = "2.0.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2c9d3793400a45f954c52e73d068316d76b6f4e36977e3fcebb13a2721e80237"
+dependencies = [
+ "crunchy",
+]
+
 [[package]]
 name = "tinystr"
 version = "0.8.2"
@@ -3465,16 +3466,6 @@ version = "0.6.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "9edde0db4769d2dc68579893f2306b26c6ecfbe0ef499b013d731b7b9247e0b9"
 
-[[package]]
-name = "xml5ever"
-version = "0.36.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f57dd51b88a4b9f99f9b55b136abb86210629d61c48117ddb87f567e51e66be7"
-dependencies = [
- "log",
- "markup5ever",
-]
-
 [[package]]
 name = "yoke"
 version = "0.8.1"
diff --git a/src/llm-coding-tools-core/Cargo.toml b/src/llm-coding-tools-core/Cargo.toml
index 5d834237..9e84d3f9 100644
--- a/src/llm-coding-tools-core/Cargo.toml
+++ b/src/llm-coding-tools-core/Cargo.toml
@@ -75,7 +75,7 @@ ignore = "0.4.25"        # Respects .gitignore when walking directories
 memchr = "2.7.6"         # Fast newline detection in read_file
 
 # Webfetch tool converts HTML to markdown for LLM-friendly output
-html-to-markdown-rs = "2.22"
+html-to-markdown-rs = "2.27"
 reqwest = { version = "0.13", default-features = false, features = [
     "rustls",
     "rustls-native-certs",