diff --git a/apps/server/src/sourceControl/AzureDevOpsSourceControlProvider.ts b/apps/server/src/sourceControl/AzureDevOpsSourceControlProvider.ts
index bf2ac9829275..2f147452f9ec 100644
--- a/apps/server/src/sourceControl/AzureDevOpsSourceControlProvider.ts
+++ b/apps/server/src/sourceControl/AzureDevOpsSourceControlProvider.ts
@@ -45,6 +45,10 @@ export const discovery = {
   executable: "az",
   versionArgs: ["--version"],
   authArgs: ["account", "show", "--query", "user.name", "-o", "tsv"],
+  // `az` boots a fresh Python interpreter on every invocation, so even `az --version`
+  // takes ~6s on Windows and overruns the default budget, leaving the provider reported
+  // as missing on machines where it is installed. `gh` and `glab` answer in ~0.3s.
+  probeTimeoutMs: 20_000,
   parseAuth: parseAzureAuth,
   installHint:
     "Install the Azure command-line tools (`az`), then enable Azure DevOps support with `az extension add --name azure-devops`.",
diff --git a/apps/server/src/sourceControl/SourceControlProviderDiscovery.ts b/apps/server/src/sourceControl/SourceControlProviderDiscovery.ts
index e3a6bd1fb205..b2b9e4513378 100644
--- a/apps/server/src/sourceControl/SourceControlProviderDiscovery.ts
+++ b/apps/server/src/sourceControl/SourceControlProviderDiscovery.ts
@@ -33,6 +33,7 @@ export type SourceControlCliDiscoverySpec = SourceControlDiscoverySpecBase & {
   readonly executable: string;
   readonly versionArgs: ReadonlyArray<string>;
   readonly authArgs: ReadonlyArray<string>;
+  readonly probeTimeoutMs?: number;
   readonly parseAuth: (input: SourceControlAuthProbeInput) => SourceControlProviderAuth;
   readonly refineUnknownRemote?: (
     input: SourceControlUnknownRemoteRefinementInput,
@@ -52,6 +53,14 @@ type SourceControlCliRemoteRefinementSpec = SourceControlCliDiscoverySpec & {
   readonly refineUnknownRemote: NonNullable<SourceControlCliDiscoverySpec["refineUnknownRemote"]>;
 };
 
+// Most provider CLIs answer `--version` in well under a second, so a short budget keeps
+// discovery snappy. Specs whose CLI is known to be slower can raise it via probeTimeoutMs.
+const DEFAULT_PROBE_TIMEOUT_MS = 5_000;
+
+function probeTimeoutMs(spec: SourceControlCliDiscoverySpec): number {
+  return spec.probeTimeoutMs ?? DEFAULT_PROBE_TIMEOUT_MS;
+}
+
 interface DiscoveryProbeResult {
   readonly kind: SourceControlProviderKind;
   readonly label: string;
@@ -167,7 +176,7 @@ function probeCli(input: {
       command: input.spec.executable,
       args: input.spec.versionArgs,
       cwd: input.cwd,
-      timeoutMs: 5_000,
+      timeoutMs: probeTimeoutMs(input.spec),
       maxOutputBytes: 8_000,
       appendTruncationMarker: true,
     })
@@ -244,7 +253,7 @@ export function probeSourceControlProvider(input: {
           args: spec.authArgs,
           cwd: input.cwd,
           allowNonZeroExit: true,
-          timeoutMs: 5_000,
+          timeoutMs: probeTimeoutMs(spec),
           maxOutputBytes: 8_000,
           appendTruncationMarker: true,
         })
@@ -287,7 +296,7 @@ export const refineUnknownRemoteProvider = Effect.fn("refineUnknownRemoteProvide
           args: spec.authArgs,
           cwd: input.cwd,
           allowNonZeroExit: true,
-          timeoutMs: 5_000,
+          timeoutMs: probeTimeoutMs(spec),
           maxOutputBytes: 8_000,
           appendTruncationMarker: true,
         })