diff --git a/acceptance/ssh/connect-serverless-feature-disabled/output.txt b/acceptance/ssh/connect-serverless-feature-disabled/output.txt
index 678cdab2437..9957a1c7e18 100644
--- a/acceptance/ssh/connect-serverless-feature-disabled/output.txt
+++ b/acceptance/ssh/connect-serverless-feature-disabled/output.txt
@@ -8,7 +8,23 @@
 >>> jq -r select(.path == "/telemetry-ext") | .body.protoLogs[] | fromjson | .entry.databricks_cli_log.ssh_tunnel_event.error_category [OUTPUT_DIR]/out.requests.txt
 DRIVER_PROXY_FORBIDDEN
 
->>> print_requests.py //api/2.2/jobs/runs/cancel
+=== Each release archive is uploaded once, and the submitted run is cancelled
+
+>>> print_requests.py //api/2.0/workspace-files/import-file //api/2.2/jobs/runs/cancel
+{
+  "method": "POST",
+  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.databricks/ssh-tunnel/[CLI_VERSION]/databricks_cli_linux_amd64/databricks.zip",
+  "q": {
+    "overwrite": "true"
+  }
+}
+{
+  "method": "POST",
+  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.databricks/ssh-tunnel/[CLI_VERSION]/databricks_cli_linux_arm64/databricks.zip",
+  "q": {
+    "overwrite": "true"
+  }
+}
 {
   "method": "POST",
   "path": "/api/2.2/jobs/runs/cancel",
diff --git a/acceptance/ssh/connect-serverless-feature-disabled/script b/acceptance/ssh/connect-serverless-feature-disabled/script
index 68bc8b23528..9f8fe5c1b92 100644
--- a/acceptance/ssh/connect-serverless-feature-disabled/script
+++ b/acceptance/ssh/connect-serverless-feature-disabled/script
@@ -18,4 +18,5 @@ add_repl "$(grep -o 'run ID: [0-9]*' out.connect.txt | grep -o '[0-9]*$')" RUN_I
 title "Reported error category\n"
 trace jq -r 'select(.path == "/telemetry-ext") | .body.protoLogs[] | fromjson | .entry.databricks_cli_log.ssh_tunnel_event.error_category' "$OUT_REQUESTS"
 
-trace print_requests.py //api/2.2/jobs/runs/cancel
+title "Each release archive is uploaded once, and the submitted run is cancelled\n"
+trace print_requests.py //api/2.0/workspace-files/import-file //api/2.2/jobs/runs/cancel
diff --git a/acceptance/ssh/connect-serverless-feature-disabled/test.toml b/acceptance/ssh/connect-serverless-feature-disabled/test.toml
index 36257965b75..3ed947e3902 100644
--- a/acceptance/ssh/connect-serverless-feature-disabled/test.toml
+++ b/acceptance/ssh/connect-serverless-feature-disabled/test.toml
@@ -1,6 +1,7 @@
 Cloud = false
 
-# Record requests so we can assert that the CLI cancels the run it submitted.
+# Record requests so we can assert that the CLI uploads each release archive once and cancels
+# the run it submitted.
 RecordRequests = true
 
 # Stand-in release archives staged by the script; not golden output.
diff --git a/experimental/ssh/internal/client/releases.go b/experimental/ssh/internal/client/releases.go
index 874a66bba2b..def34ce363c 100644
--- a/experimental/ssh/internal/client/releases.go
+++ b/experimental/ssh/internal/client/releases.go
@@ -121,6 +121,11 @@ func uploadReleases(ctx context.Context, workspaceFiler filer.Filer, getRelease
 			}
 		}
 
+		err := workspaceFiler.Mkdir(ctx, remoteSubFolder)
+		if err != nil {
+			return fmt.Errorf("failed to create directory %s in workspace: %w", remoteSubFolder, err)
+		}
+
 		releaseReader, err := getRelease(ctx, arch, version, releasesDir)
 		if err != nil {
 			return fmt.Errorf("failed to get archive for architecture %s: %w", arch, err)
diff --git a/experimental/ssh/internal/client/releases_test.go b/experimental/ssh/internal/client/releases_test.go
index 81984741834..e0e2c384d9d 100644
--- a/experimental/ssh/internal/client/releases_test.go
+++ b/experimental/ssh/internal/client/releases_test.go
@@ -6,11 +6,15 @@ import (
 	"fmt"
 	"io"
 	"net/http"
+	"path"
 	"strings"
+	"sync"
 	"syscall"
 	"testing"
 
 	"github.com/databricks/cli/libs/filer"
+	"github.com/databricks/cli/libs/testserver"
+	"github.com/databricks/databricks-sdk-go"
 	"github.com/databricks/databricks-sdk-go/apierr"
 	"github.com/databricks/databricks-sdk-go/config"
 	"github.com/stretchr/testify/assert"
@@ -141,3 +145,69 @@ func TestUploadReleasesWithExistingBinary(t *testing.T) {
 		})
 	}
 }
+
+func TestUploadReleasesSendsEachArchiveOnce(t *testing.T) {
+	tests := []struct {
+		name    string
+		version string
+		uploads int
+		want    []string
+	}{
+		{
+			name:    "release version into new folders",
+			version: "1.12.0",
+			uploads: 1,
+			want: []string{
+				"databricks_cli_1.12.0_linux_amd64 200",
+				"databricks_cli_1.12.0_linux_arm64 200",
+			},
+		},
+		{
+			name:    "dev version again into existing folders",
+			version: "1.12.1-dev+abcdef123456",
+			uploads: 2,
+			want: []string{
+				"databricks_cli_linux_amd64 200",
+				"databricks_cli_linux_arm64 200",
+				"databricks_cli_linux_amd64 200",
+				"databricks_cli_linux_arm64 200",
+			},
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			server := testserver.New(t)
+			testserver.AddDefaultHandlers(server)
+			var mu sync.Mutex
+			var imports []string
+			server.ResponseCallback = func(req *testserver.Request, resp *testserver.EncodedResponse) {
+				if !strings.HasPrefix(req.URL.Path, "/api/2.0/workspace-files/import-file/") {
+					return
+				}
+				mu.Lock()
+				defer mu.Unlock()
+				imports = append(imports, fmt.Sprintf("%s %d", path.Base(path.Dir(req.URL.Path)), resp.StatusCode))
+			}
+			client, err := databricks.NewWorkspaceClient(&databricks.Config{
+				Host:  server.URL,
+				Token: "testtoken",
+			})
+			require.NoError(t, err)
+			workspaceFiler, err := filer.NewWorkspaceFilesClient(client, "/Workspace/Users/tester@databricks.test/.databricks/ssh-tunnel/"+tt.version)
+			require.NoError(t, err)
+
+			getRelease := func(ctx context.Context, architecture, version, releasesDir string) (io.ReadCloser, error) {
+				return io.NopCloser(strings.NewReader("archive")), nil
+			}
+			for range tt.uploads {
+				err = uploadReleases(t.Context(), workspaceFiler, getRelease, tt.version, "")
+				require.NoError(t, err)
+			}
+
+			mu.Lock()
+			defer mu.Unlock()
+			assert.Equal(t, tt.want, imports)
+		})
+	}
+}