diff --git a/python/copilot/generated/rpc.py b/python/copilot/generated/rpc.py
index 500a16eb7..84f21db7e 100644
--- a/python/copilot/generated/rpc.py
+++ b/python/copilot/generated/rpc.py
@@ -7391,7 +7391,7 @@ class QueuedCommandHandled:
     """Queued-command response indicating the host executed the command, with an optional flag
     to stop queue processing.
     """
-    handled: ClassVar[str] = "true"
+    handled: ClassVar[bool] = True
     """The host actually executed the queued command."""
 
     stop_processing_queue: bool | None = None
@@ -7418,7 +7418,7 @@ class QueuedCommandNotHandled:
     """Queued-command response indicating the host did not execute the command and the queue may
     continue.
     """
-    handled: ClassVar[str] = "false"
+    handled: ClassVar[bool] = False
     """The host did not execute the queued command. Unblocks the queue without claiming the
     command was processed (e.g. when the handler threw before completing).
     """
@@ -31183,8 +31183,8 @@ def _load_QueuedCommandResult(obj: Any) -> "QueuedCommandResult":
     assert isinstance(obj, dict)
     kind = obj.get("handled")
     match kind:
-        case "true": return QueuedCommandHandled.from_dict(obj)
-        case "false": return QueuedCommandNotHandled.from_dict(obj)
+        case True: return QueuedCommandHandled.from_dict(obj)
+        case False: return QueuedCommandNotHandled.from_dict(obj)
         case _: raise ValueError(f"Unknown QueuedCommandResult handled: {kind!r}")
 
 # State of the runtime-managed remote-control singleton.
@@ -31207,8 +31207,8 @@ def _load_SessionListEntry(obj: Any) -> "SessionListEntry":
     assert isinstance(obj, dict)
     kind = obj.get("isRemote")
     match kind:
-        case "false": return LocalSessionMetadataValue.from_dict(obj)
-        case "true": return RemoteSessionMetadataValue.from_dict(obj)
+        case False: return LocalSessionMetadataValue.from_dict(obj)
+        case True: return RemoteSessionMetadataValue.from_dict(obj)
         case _: raise ValueError(f"Unknown SessionListEntry isRemote: {kind!r}")
 
 # Open a session by creating, resuming, attaching, connecting to a remote, or handing off.
diff --git a/python/test_rpc_generated.py b/python/test_rpc_generated.py
index 8b9423c13..2f3f78060 100644
--- a/python/test_rpc_generated.py
+++ b/python/test_rpc_generated.py
@@ -4,9 +4,15 @@
 
 import pytest
 
+from copilot.generated.rpc import _load_SessionListEntry
 from copilot.rpc import (
     CommandsApi,
     CommandsInvokeRequest,
+    LocalSessionMetadataValue,
+    QueuedCommandHandled,
+    QueuedCommandNotHandled,
+    RemoteSessionMetadataValue,
+    SessionList,
     SlashCommandTextResult,
 )
 
@@ -22,3 +28,48 @@ async def test_commands_invoke_deserializes_slash_command_result():
     assert isinstance(result, SlashCommandTextResult)
     assert result.text == "hello"
     assert result.markdown is True
+
+
+def test_session_list_entry_decodes_boolean_is_remote_discriminator():
+    local_payload = {
+        "sessionId": "example-local",
+        "startTime": "2026-07-26T10:00:00.000Z",
+        "modifiedTime": "2026-07-26T10:05:00.000Z",
+        "isRemote": False,
+    }
+    remote_payload = {
+        "sessionId": "example-remote",
+        "startTime": "2026-07-26T10:00:00.000Z",
+        "modifiedTime": "2026-07-26T10:05:00.000Z",
+        "isRemote": True,
+        "remoteSessionIds": ["rs-1"],
+        "repository": {
+            "owner": "github",
+            "name": "copilot-sdk",
+            "branch": "main",
+        },
+    }
+
+    local_entry = _load_SessionListEntry(local_payload)
+    remote_entry = _load_SessionListEntry(remote_payload)
+
+    assert isinstance(local_entry, LocalSessionMetadataValue)
+    assert local_entry.session_id == "example-local"
+    assert isinstance(remote_entry, RemoteSessionMetadataValue)
+    assert remote_entry.session_id == "example-remote"
+
+    session_list = SessionList.from_dict({"sessions": [local_payload, remote_payload]})
+    assert len(session_list.sessions) == 2
+    assert isinstance(session_list.sessions[0], LocalSessionMetadataValue)
+    assert isinstance(session_list.sessions[1], RemoteSessionMetadataValue)
+
+
+def test_queued_command_result_round_trips_boolean_handled_discriminator():
+    handled = QueuedCommandHandled(stop_processing_queue=True)
+    not_handled = QueuedCommandNotHandled()
+
+    assert handled.to_dict() == {"handled": True, "stopProcessingQueue": True}
+    assert not_handled.to_dict() == {"handled": False}
+
+    assert QueuedCommandHandled.from_dict({"handled": True, "stopProcessingQueue": True}) == handled
+    assert QueuedCommandNotHandled.from_dict({"handled": False}) == not_handled
diff --git a/scripts/codegen/python.ts b/scripts/codegen/python.ts
index 5b343122b..b6ce16ad8 100644
--- a/scripts/codegen/python.ts
+++ b/scripts/codegen/python.ts
@@ -272,6 +272,33 @@ function postProcessExternalUnionAliasesForPython(code: string, aliases: Map<str
     return code.replace(/\n{3,}/g, "\n\n");
 }
 
+type PyDiscriminatorValue = string | boolean;
+
+function pyDiscriminatorConstValue(schema: JSONSchema7): PyDiscriminatorValue | undefined {
+    if (typeof schema.const === "string" || typeof schema.const === "boolean") {
+        return schema.const;
+    }
+    return undefined;
+}
+
+function pyDiscriminatorMatchPattern(value: PyDiscriminatorValue): string {
+    if (typeof value === "boolean") {
+        return value ? "True" : "False";
+    }
+    return JSON.stringify(value);
+}
+
+function pyDiscriminatorLiteral(value: PyDiscriminatorValue): string {
+    if (typeof value === "boolean") {
+        return value ? "True" : "False";
+    }
+    return JSON.stringify(value);
+}
+
+function pyDiscriminatorClassVarType(value: PyDiscriminatorValue): "str" | "bool" {
+    return typeof value === "boolean" ? "bool" : "str";
+}
+
 /**
  * Replace flat-merged dataclasses emitted by quicktype for $ref-based
  * discriminated unions with proper Python unions: a `Name = VariantA | ...`
@@ -293,7 +320,7 @@ function postProcessExternalUnionAliasesForPython(code: string, aliases: Map<str
 interface ResolvedRefBasedUnion {
     aliasName: string;
     discriminatorProp: string;
-    dispatch: Array<{ value: string; typeName: string }>;
+    dispatch: Array<{ value: PyDiscriminatorValue; typeName: string }>;
 }
 function postProcessRefBasedDiscriminatedUnionsForPython(
     code: string,
@@ -304,7 +331,7 @@ function postProcessRefBasedDiscriminatedUnionsForPython(
         aliasName: string;
         variantNames: string[];
         discriminatorProp: string;
-        dispatch: Array<{ value: string; typeName: string }>;
+        dispatch: Array<{ value: PyDiscriminatorValue; typeName: string }>;
         description: string | undefined;
     }
     const unions: UnionInfo[] = [];
@@ -333,8 +360,12 @@ function postProcessRefBasedDiscriminatedUnionsForPython(
             const discProp = (resolvedVariants[i].properties as Record<string, JSONSchema7>)[
                 discriminator.property
             ];
+            const discValue = pyDiscriminatorConstValue(discProp);
+            if (discValue === undefined) {
+                throw new Error(`Missing discriminator const on ${variantRefNames[i]}`);
+            }
             return {
-                value: String(discProp.const),
+                value: discValue,
                 typeName: toPascalCase(variantRefNames[i]),
             };
         });
@@ -387,7 +418,7 @@ function postProcessRefBasedDiscriminatedUnionsForPython(
     for (const union of unions) {
         const actualAliasName = resolveActualName(union.aliasName);
         const actualVariantNames: string[] = [];
-        const actualDispatch: Array<{ value: string; typeName: string }> = [];
+        const actualDispatch: Array<{ value: PyDiscriminatorValue; typeName: string }> = [];
         let allResolved = true;
         for (let i = 0; i < union.variantNames.length; i++) {
             const actual = resolveActualName(union.variantNames[i]);
@@ -450,7 +481,9 @@ function postProcessRefBasedDiscriminatedUnionsForPython(
         dispatcherLines.push(`    kind = obj.get(${JSON.stringify(union.discriminatorProp)})`);
         dispatcherLines.push(`    match kind:`);
         for (const m of actualDispatch) {
-            dispatcherLines.push(`        case ${JSON.stringify(m.value)}: return ${m.typeName}.from_dict(obj)`);
+            dispatcherLines.push(
+                `        case ${pyDiscriminatorMatchPattern(m.value)}: return ${m.typeName}.from_dict(obj)`
+            );
         }
         dispatcherLines.push(
             `        case _: raise ValueError(f"Unknown ${actualAliasName} ${union.discriminatorProp}: {kind!r}")`
@@ -500,7 +533,7 @@ function postProcessDiscriminatorDefaultsForPython(
     unions: ResolvedRefBasedUnion[]
 ): string {
     // Build variant lookup: variant class name → { prop, value }.
-    const variantInfo = new Map<string, { prop: string; value: string }>();
+    const variantInfo = new Map<string, { prop: string; value: PyDiscriminatorValue }>();
     for (const union of unions) {
         for (const d of union.dispatch) {
             // First-wins; multiple unions referencing the same variant share a
@@ -571,9 +604,10 @@ function postProcessDiscriminatorDefaultsForPython(
             continue;
         }
         const fieldIndent = (block[fieldIdx].match(/^(\s+)/) ?? ["", ""])[1];
-        const literal = JSON.stringify(info.value);
+        const literal = pyDiscriminatorLiteral(info.value);
+        const classVarType = pyDiscriminatorClassVarType(info.value);
         // Replace the field with a class-level constant.
-        block[fieldIdx] = `${fieldIndent}${info.prop}: ClassVar[str] = ${literal}`;
+        block[fieldIdx] = `${fieldIndent}${info.prop}: ClassVar[${classVarType}] = ${literal}`;
         usedClassVar = true;
 
         // Drop any field-trailing docstring lines that immediately followed the
@@ -1590,7 +1624,7 @@ function tryEmitPyRefBasedDiscriminatedUnion(
     if (!discriminator) return undefined;
 
     const variantTypeNames: string[] = [];
-    const dispatch: Array<{ value: string; typeName: string }> = [];
+    const dispatch: Array<{ value: PyDiscriminatorValue; typeName: string }> = [];
     for (let i = 0; i < variants.length; i++) {
         const variantTypeName = toPascalCase(variantRefNames[i]);
         const variantSchema = resolveObjectSchema(variants[i], ctx.definitions);
@@ -1599,7 +1633,11 @@ function tryEmitPyRefBasedDiscriminatedUnion(
         }
         variantTypeNames.push(variantTypeName);
         const discProp = resolvedVariants[i].properties?.[discriminator.property] as JSONSchema7;
-        dispatch.push({ value: String(discProp.const), typeName: variantTypeName });
+        const discValue = pyDiscriminatorConstValue(discProp);
+        if (discValue === undefined) {
+            throw new Error(`Missing discriminator const on ${variantRefNames[i]}`);
+        }
+        dispatch.push({ value: discValue, typeName: variantTypeName });
     }
 
     if (!ctx.aliasesByName.has(aliasName)) {
@@ -1627,7 +1665,7 @@ function tryEmitPyRefBasedDiscriminatedUnion(
         lines.push(`    match kind:`);
         for (const m of dispatch) {
             lines.push(
-                `        case ${JSON.stringify(m.value)}: return ${m.typeName}.from_dict(obj)`
+                `        case ${pyDiscriminatorMatchPattern(m.value)}: return ${m.typeName}.from_dict(obj)`
             );
         }
         lines.push(