diff --git a/Cargo.lock b/Cargo.lock
index 42454453c..33f8b6f68 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -4966,12 +4966,11 @@ dependencies = [
 
 [[package]]
 name = "rustyline"
-version = "18.0.1"
+version = "19.0.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "53f6a737db68eb1a8ccff86b584b2fc13eca6a7bb6f78ebc7c529547e3ab9684"
+checksum = "56e1d6bd81c2d5feafd2419138df9183c45a10a492c4e873b8b0acb8eb2b549e"
 dependencies = [
  "bitflags 2.13.2",
- "cfg-if",
  "clipboard-win",
  "home",
  "libc",
@@ -5667,7 +5666,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "32497e9a4c7b38532efcdebeef879707aa9f794296a4f0244f6f69e9bc8574bd"
 dependencies = [
  "fastrand",
- "getrandom 0.3.4",
+ "getrandom 0.4.3",
  "once_cell",
  "rustix",
  "windows-sys 0.61.2",
diff --git a/crates/bashkit-cli/Cargo.toml b/crates/bashkit-cli/Cargo.toml
index 7dc458e93..a8967167a 100644
--- a/crates/bashkit-cli/Cargo.toml
+++ b/crates/bashkit-cli/Cargo.toml
@@ -43,7 +43,7 @@ bashkit = { path = "../bashkit", version = "0.19.0", default-features = false, f
 tokio = { workspace = true, features = ["macros", "net", "rt", "rt-multi-thread", "time", "io-std"] }
 clap.workspace = true
 anyhow.workspace = true
-rustyline = { version = "18", optional = true }
+rustyline = { version = "19", optional = true }
 terminal_size = { version = "0.4", optional = true }
 signal-hook = { version = "0.4", optional = true }
 
diff --git a/knowledge/integrations/interactive-shell.md b/knowledge/integrations/interactive-shell.md
index 08885fd75..45634ba9c 100644
--- a/knowledge/integrations/interactive-shell.md
+++ b/knowledge/integrations/interactive-shell.md
@@ -74,7 +74,10 @@ Completes based on context:
 - Directories show trailing `/`
 
 Uses rustyline `Completer` trait with `CompletionType::List` (shows
-all matches on tab).
+all matches on tab). From rustyline 19, the "display all N
+possibilities?" prompt that `List` shows for a large match set accepts
+Tab as confirmation alongside `y`/`n` (rustyline #955), so a second Tab
+no longer falls through as a rejected keypress.
 
 #### History Hints
 
diff --git a/supply-chain/config.toml b/supply-chain/config.toml
index f71744dd7..94c7631a0 100644
--- a/supply-chain/config.toml
+++ b/supply-chain/config.toml
@@ -1664,7 +1664,7 @@ version = "0.3.1"
 criteria = "safe-to-run"
 
 [[exemptions.rustyline]]
-version = "18.0.1"
+version = "19.0.0"
 criteria = "safe-to-deploy"
 
 [[exemptions.ryu]]