diff --git a/acceptance/bundle/multi_profile/auto_select/.databrickscfg b/acceptance/bundle/multi_profile/auto_select/.databrickscfg
new file mode 100644
index 0000000000..5fc2fc87a6
--- /dev/null
+++ b/acceptance/bundle/multi_profile/auto_select/.databrickscfg
@@ -0,0 +1,8 @@
+[ws-profile]
+host = $DATABRICKS_HOST
+token = $DATABRICKS_TOKEN
+
+[acc-profile]
+host = $DATABRICKS_HOST
+account_id = abc123
+token = acc-token
diff --git a/acceptance/bundle/multi_profile/auto_select/databricks.yml b/acceptance/bundle/multi_profile/auto_select/databricks.yml
new file mode 100644
index 0000000000..50ac852b94
--- /dev/null
+++ b/acceptance/bundle/multi_profile/auto_select/databricks.yml
@@ -0,0 +1,2 @@
+bundle:
+  name: multi-profile-auto-select
diff --git a/acceptance/bundle/multi_profile/auto_select/out.test.toml b/acceptance/bundle/multi_profile/auto_select/out.test.toml
new file mode 100644
index 0000000000..d560f1de04
--- /dev/null
+++ b/acceptance/bundle/multi_profile/auto_select/out.test.toml
@@ -0,0 +1,5 @@
+Local = true
+Cloud = false
+
+[EnvMatrix]
+  DATABRICKS_BUNDLE_ENGINE = ["terraform", "direct"]
diff --git a/acceptance/bundle/multi_profile/auto_select/output.txt b/acceptance/bundle/multi_profile/auto_select/output.txt
new file mode 100644
index 0000000000..4140d9ff34
--- /dev/null
+++ b/acceptance/bundle/multi_profile/auto_select/output.txt
@@ -0,0 +1,5 @@
+
+>>> [CLI] bundle validate -o json
+{
+  "name": "multi-profile-auto-select"
+}
diff --git a/acceptance/bundle/multi_profile/auto_select/script b/acceptance/bundle/multi_profile/auto_select/script
new file mode 100644
index 0000000000..c785d4e0b4
--- /dev/null
+++ b/acceptance/bundle/multi_profile/auto_select/script
@@ -0,0 +1,21 @@
+# Set up .databrickscfg with two profiles for the same host:
+# one workspace profile and one account profile.
+envsubst < .databrickscfg > out && mv out .databrickscfg
+
+# Write databricks.yml with the actual host URL.
+cat > databricks.yml << EOF
+bundle:
+  name: multi-profile-auto-select
+
+workspace:
+  host: $DATABRICKS_HOST
+EOF
+
+export DATABRICKS_CONFIG_FILE=.databrickscfg
+unset DATABRICKS_HOST
+unset DATABRICKS_TOKEN
+
+# Only one workspace-compatible profile exists (ws-profile).
+# The account-only profile (acc-profile) is filtered out.
+# Auto-select happens silently and validate succeeds.
+trace $CLI bundle validate -o json | jq '{name: .bundle.name}'
diff --git a/acceptance/bundle/multi_profile/env_auth_skip/.databrickscfg b/acceptance/bundle/multi_profile/env_auth_skip/.databrickscfg
new file mode 100644
index 0000000000..d0825fa0d7
--- /dev/null
+++ b/acceptance/bundle/multi_profile/env_auth_skip/.databrickscfg
@@ -0,0 +1,7 @@
+[profile-1]
+host = $DATABRICKS_HOST
+token = t1
+
+[profile-2]
+host = $DATABRICKS_HOST
+token = t2
diff --git a/acceptance/bundle/multi_profile/env_auth_skip/databricks.yml b/acceptance/bundle/multi_profile/env_auth_skip/databricks.yml
new file mode 100644
index 0000000000..cc3be2a1dc
--- /dev/null
+++ b/acceptance/bundle/multi_profile/env_auth_skip/databricks.yml
@@ -0,0 +1,2 @@
+bundle:
+  name: multi-profile-env-skip
diff --git a/acceptance/bundle/multi_profile/env_auth_skip/out.test.toml b/acceptance/bundle/multi_profile/env_auth_skip/out.test.toml
new file mode 100644
index 0000000000..d560f1de04
--- /dev/null
+++ b/acceptance/bundle/multi_profile/env_auth_skip/out.test.toml
@@ -0,0 +1,5 @@
+Local = true
+Cloud = false
+
+[EnvMatrix]
+  DATABRICKS_BUNDLE_ENGINE = ["terraform", "direct"]
diff --git a/acceptance/bundle/multi_profile/env_auth_skip/output.txt b/acceptance/bundle/multi_profile/env_auth_skip/output.txt
new file mode 100644
index 0000000000..cff59934e0
--- /dev/null
+++ b/acceptance/bundle/multi_profile/env_auth_skip/output.txt
@@ -0,0 +1,5 @@
+
+>>> [CLI] bundle validate -o json
+{
+  "name": "multi-profile-env-skip"
+}
diff --git a/acceptance/bundle/multi_profile/env_auth_skip/script b/acceptance/bundle/multi_profile/env_auth_skip/script
new file mode 100644
index 0000000000..5f934dfc10
--- /dev/null
+++ b/acceptance/bundle/multi_profile/env_auth_skip/script
@@ -0,0 +1,16 @@
+# Set up .databrickscfg with two workspace profiles for the same host.
+envsubst < .databrickscfg > out && mv out .databrickscfg
+
+cat > databricks.yml << EOF
+bundle:
+  name: multi-profile-env-skip
+
+workspace:
+  host: $DATABRICKS_HOST
+EOF
+
+export DATABRICKS_CONFIG_FILE=.databrickscfg
+# Keep DATABRICKS_HOST and DATABRICKS_TOKEN set — env auth takes precedence
+# over host-based profile matching, so errMultipleProfiles never fires.
+
+trace $CLI bundle validate -o json | jq '{name: .bundle.name}'
diff --git a/acceptance/bundle/multi_profile/no_workspace_profiles/.databrickscfg b/acceptance/bundle/multi_profile/no_workspace_profiles/.databrickscfg
new file mode 100644
index 0000000000..18253c223e
--- /dev/null
+++ b/acceptance/bundle/multi_profile/no_workspace_profiles/.databrickscfg
@@ -0,0 +1,9 @@
+[acc-1]
+host = $DATABRICKS_HOST
+account_id = abc
+token = t1
+
+[acc-2]
+host = $DATABRICKS_HOST
+account_id = def
+token = t2
diff --git a/acceptance/bundle/multi_profile/no_workspace_profiles/databricks.yml b/acceptance/bundle/multi_profile/no_workspace_profiles/databricks.yml
new file mode 100644
index 0000000000..298f0763d7
--- /dev/null
+++ b/acceptance/bundle/multi_profile/no_workspace_profiles/databricks.yml
@@ -0,0 +1,2 @@
+bundle:
+  name: multi-profile-no-ws
diff --git a/acceptance/bundle/multi_profile/no_workspace_profiles/out.test.toml b/acceptance/bundle/multi_profile/no_workspace_profiles/out.test.toml
new file mode 100644
index 0000000000..d560f1de04
--- /dev/null
+++ b/acceptance/bundle/multi_profile/no_workspace_profiles/out.test.toml
@@ -0,0 +1,5 @@
+Local = true
+Cloud = false
+
+[EnvMatrix]
+  DATABRICKS_BUNDLE_ENGINE = ["terraform", "direct"]
diff --git a/acceptance/bundle/multi_profile/no_workspace_profiles/output.txt b/acceptance/bundle/multi_profile/no_workspace_profiles/output.txt
new file mode 100644
index 0000000000..02a544efb5
--- /dev/null
+++ b/acceptance/bundle/multi_profile/no_workspace_profiles/output.txt
@@ -0,0 +1,12 @@
+
+>>> [CLI] bundle validate
+Error: cannot resolve bundle auth configuration: resolve: [DATABRICKS_URL]: multiple profiles matched: acc-1, acc-2: please set DATABRICKS_CONFIG_PROFILE or provide --profile flag to specify one. Config: host=[DATABRICKS_URL], config_file=.databrickscfg, databricks_cli_path=[CLI]. Env: DATABRICKS_CONFIG_FILE, DATABRICKS_CLI_PATH
+
+Name: multi-profile-no-ws
+Target: default
+Workspace:
+  Host: [DATABRICKS_URL]
+
+Found 1 error
+
+Exit code: 1
diff --git a/acceptance/bundle/multi_profile/no_workspace_profiles/script b/acceptance/bundle/multi_profile/no_workspace_profiles/script
new file mode 100644
index 0000000000..97dda0e2af
--- /dev/null
+++ b/acceptance/bundle/multi_profile/no_workspace_profiles/script
@@ -0,0 +1,17 @@
+# Set up .databrickscfg with two account-only profiles for the same host.
+envsubst < .databrickscfg > out && mv out .databrickscfg
+
+cat > databricks.yml << EOF
+bundle:
+  name: multi-profile-no-ws
+
+workspace:
+  host: $DATABRICKS_HOST
+EOF
+
+export DATABRICKS_CONFIG_FILE=.databrickscfg
+unset DATABRICKS_HOST
+unset DATABRICKS_TOKEN
+
+# No workspace-compatible profiles → original multi-profile error returned.
+errcode trace $CLI bundle validate
diff --git a/acceptance/bundle/multi_profile/non_interactive_error/.databrickscfg b/acceptance/bundle/multi_profile/non_interactive_error/.databrickscfg
new file mode 100644
index 0000000000..d0825fa0d7
--- /dev/null
+++ b/acceptance/bundle/multi_profile/non_interactive_error/.databrickscfg
@@ -0,0 +1,7 @@
+[profile-1]
+host = $DATABRICKS_HOST
+token = t1
+
+[profile-2]
+host = $DATABRICKS_HOST
+token = t2
diff --git a/acceptance/bundle/multi_profile/non_interactive_error/databricks.yml b/acceptance/bundle/multi_profile/non_interactive_error/databricks.yml
new file mode 100644
index 0000000000..529bc314c7
--- /dev/null
+++ b/acceptance/bundle/multi_profile/non_interactive_error/databricks.yml
@@ -0,0 +1,2 @@
+bundle:
+  name: multi-profile-non-interactive
diff --git a/acceptance/bundle/multi_profile/non_interactive_error/out.test.toml b/acceptance/bundle/multi_profile/non_interactive_error/out.test.toml
new file mode 100644
index 0000000000..d560f1de04
--- /dev/null
+++ b/acceptance/bundle/multi_profile/non_interactive_error/out.test.toml
@@ -0,0 +1,5 @@
+Local = true
+Cloud = false
+
+[EnvMatrix]
+  DATABRICKS_BUNDLE_ENGINE = ["terraform", "direct"]
diff --git a/acceptance/bundle/multi_profile/non_interactive_error/output.txt b/acceptance/bundle/multi_profile/non_interactive_error/output.txt
new file mode 100644
index 0000000000..d3621f1274
--- /dev/null
+++ b/acceptance/bundle/multi_profile/non_interactive_error/output.txt
@@ -0,0 +1,23 @@
+
+>>> [CLI] bundle validate
+Error: cannot resolve bundle auth configuration: resolve: [DATABRICKS_URL]: multiple profiles matched: profile-1, profile-2: please set DATABRICKS_CONFIG_PROFILE or provide --profile flag to specify one. Config: host=[DATABRICKS_URL], config_file=.databrickscfg, databricks_cli_path=[CLI]. Env: DATABRICKS_CONFIG_FILE, DATABRICKS_CLI_PATH
+
+Matching workspace profiles: profile-1, profile-2
+
+Fix (pick one):
+  1. Set profile in databricks.yml:
+       workspace:
+         profile: profile-1
+  2. Pass a flag:
+       databricks bundle validate --profile profile-1
+  3. Set env var:
+       DATABRICKS_CONFIG_PROFILE=profile-1
+
+Name: multi-profile-non-interactive
+Target: default
+Workspace:
+  Host: [DATABRICKS_URL]
+
+Found 1 error
+
+Exit code: 1
diff --git a/acceptance/bundle/multi_profile/non_interactive_error/script b/acceptance/bundle/multi_profile/non_interactive_error/script
new file mode 100644
index 0000000000..85003ad471
--- /dev/null
+++ b/acceptance/bundle/multi_profile/non_interactive_error/script
@@ -0,0 +1,17 @@
+# Set up .databrickscfg with two workspace profiles for the same host.
+envsubst < .databrickscfg > out && mv out .databrickscfg
+
+cat > databricks.yml << EOF
+bundle:
+  name: multi-profile-non-interactive
+
+workspace:
+  host: $DATABRICKS_HOST
+EOF
+
+export DATABRICKS_CONFIG_FILE=.databrickscfg
+unset DATABRICKS_HOST
+unset DATABRICKS_TOKEN
+
+# Multiple workspace profiles, non-interactive → error with guidance.
+errcode trace $CLI bundle validate
diff --git a/acceptance/bundle/multi_profile/test.toml b/acceptance/bundle/multi_profile/test.toml
new file mode 100644
index 0000000000..85e02532c9
--- /dev/null
+++ b/acceptance/bundle/multi_profile/test.toml
@@ -0,0 +1,3 @@
+Local = true
+Cloud = false
+Ignore = [".databricks"]
diff --git a/bundle/bundle.go b/bundle/bundle.go
index f5a258a013..b2dae07554 100644
--- a/bundle/bundle.go
+++ b/bundle/bundle.go
@@ -245,6 +245,14 @@ func (b *Bundle) SetWorkpaceClient(w *databricks.WorkspaceClient) {
 	b.client = w
 }
 
+// ClearWorkspaceClient resets the workspace client cache, allowing
+// WorkspaceClientE() to attempt client creation again on the next call.
+func (b *Bundle) ClearWorkspaceClient() {
+	b.clientOnce = sync.Once{}
+	b.client = nil
+	b.clientErr = nil
+}
+
 // LocalStateDir returns directory to use for temporary files for this bundle without creating
 // Scoped to the bundle's target.
 func (b *Bundle) GetLocalStateDir(ctx context.Context, paths ...string) string {
diff --git a/bundle/bundle_test.go b/bundle/bundle_test.go
index 9cc9c4de4b..5b2aff58e0 100644
--- a/bundle/bundle_test.go
+++ b/bundle/bundle_test.go
@@ -179,3 +179,28 @@ func TestBundleGetResourceConfigJobsPointer(t *testing.T) {
 	require.EqualError(t, err, "no such resource type in the config: \"not_found\"")
 	require.Nil(t, res)
 }
+
+func TestClearWorkspaceClient(t *testing.T) {
+	// First attempt: profile "profile-A" doesn't exist → error mentions "profile-A".
+	b := &Bundle{}
+	b.Config.Workspace.Host = "https://nonexistent.example.com"
+	b.Config.Workspace.Profile = "profile-A"
+
+	_, err1 := b.WorkspaceClientE()
+	require.Error(t, err1)
+	assert.Contains(t, err1.Error(), "profile-A")
+
+	// Without retry, second call returns the same cached error (same object).
+	_, err1b := b.WorkspaceClientE()
+	assert.Same(t, err1, err1b, "expected same cached error without retry")
+
+	// After retry, change the profile to "profile-B" and call again.
+	// If retry didn't re-execute, the error would still mention "profile-A".
+	b.ClearWorkspaceClient()
+	b.Config.Workspace.Profile = "profile-B"
+
+	_, err2 := b.WorkspaceClientE()
+	require.Error(t, err2)
+	assert.Contains(t, err2.Error(), "profile-B", "expected re-execution to pick up new profile")
+	assert.NotContains(t, err2.Error(), "profile-A", "stale cached error should not appear")
+}
diff --git a/cmd/root/auth.go b/cmd/root/auth.go
index 2ae0789eda..60360bd3e6 100644
--- a/cmd/root/auth.go
+++ b/cmd/root/auth.go
@@ -234,6 +234,27 @@ func MustWorkspaceClient(cmd *cobra.Command, args []string) error {
 	return nil
 }
 
+// promptForProfileByHost prompts the user to select a profile when multiple
+// profiles match the same host.
+func promptForProfileByHost(ctx context.Context, profiles profile.Profiles, host string) (string, error) {
+	i, _, err := cmdio.RunSelect(ctx, &promptui.Select{
+		Label:             "Multiple profiles match host " + host,
+		Items:             profiles,
+		Searcher:          profiles.SearchCaseInsensitive,
+		StartInSearchMode: true,
+		Templates: &promptui.SelectTemplates{
+			Label:    "{{ . | faint }}",
+			Active:   `{{.Name | bold}}{{if .AccountID}} (account: {{.AccountID|faint}}){{end}}{{if .WorkspaceID}} (workspace: {{.WorkspaceID|faint}}){{end}}`,
+			Inactive: `{{.Name}}{{if .AccountID}} (account: {{.AccountID}}){{end}}{{if .WorkspaceID}} (workspace: {{.WorkspaceID}}){{end}}`,
+			Selected: `{{ "Using profile" | faint }}: {{ .Name | bold }}`,
+		},
+	})
+	if err != nil {
+		return "", err
+	}
+	return profiles[i].Name, nil
+}
+
 func AskForWorkspaceProfile(ctx context.Context) (string, error) {
 	profiler := profile.GetProfiler(ctx)
 	path, err := profiler.GetPath(ctx)
diff --git a/cmd/root/bundle.go b/cmd/root/bundle.go
index 3876b7fec4..123990acff 100644
--- a/cmd/root/bundle.go
+++ b/cmd/root/bundle.go
@@ -2,11 +2,17 @@ package root
 
 import (
 	"context"
+	"errors"
+	"fmt"
+	"strings"
 
 	"github.com/databricks/cli/bundle"
 	"github.com/databricks/cli/bundle/env"
 	"github.com/databricks/cli/bundle/phases"
 	"github.com/databricks/cli/libs/cmdctx"
+	"github.com/databricks/cli/libs/cmdio"
+	"github.com/databricks/cli/libs/databrickscfg"
+	"github.com/databricks/cli/libs/databrickscfg/profile"
 	envlib "github.com/databricks/cli/libs/env"
 	"github.com/databricks/cli/libs/logdiag"
 	"github.com/spf13/cobra"
@@ -72,6 +78,60 @@ func configureProfile(cmd *cobra.Command, b *bundle.Bundle) {
 	})
 }
 
+// resolveProfileAmbiguity resolves a multi-profile match by filtering to
+// workspace-compatible profiles and either auto-selecting, prompting, or
+// returning a guidance error.
+func resolveProfileAmbiguity(cmd *cobra.Command, b *bundle.Bundle, originalErr error, names []string) (string, error) {
+	ctx := cmd.Context()
+
+	namesMatcher := profile.MatchProfileNames(names...)
+	profiler := profile.GetProfiler(ctx)
+	profiles, err := profiler.LoadProfiles(ctx, func(p profile.Profile) bool {
+		return namesMatcher(p) && profile.MatchWorkspaceProfiles(p)
+	})
+	if err != nil {
+		if errors.Is(err, profile.ErrNoConfiguration) {
+			return "", originalErr
+		}
+		return "", err
+	}
+
+	switch len(profiles) {
+	case 0:
+		return "", originalErr
+	case 1:
+		// Exactly one workspace-compatible profile — auto-select.
+		// This happens when multiple profiles match a host but only one
+		// is workspace-compatible (the rest are account-only).
+		return profiles[0].Name, nil
+	}
+
+	// Multiple workspace-compatible profiles — need interactive selection.
+	_, hasProfileFlag := profileFlagValue(cmd)
+	allowPrompt := !hasProfileFlag && !shouldSkipPrompt(ctx)
+	if !allowPrompt || !cmdio.IsPromptSupported(ctx) {
+		return "", fmt.Errorf(
+			"%w\n\nMatching workspace profiles: %s\n\n"+
+				"Fix (pick one):\n"+
+				"  1. Set profile in databricks.yml:\n"+
+				"       workspace:\n"+
+				"         profile: %s\n"+
+				"  2. Pass a flag:\n"+
+				"       %s --profile %s\n"+
+				"  3. Set env var:\n"+
+				"       DATABRICKS_CONFIG_PROFILE=%s",
+			originalErr,
+			strings.Join(profiles.Names(), ", "),
+			profiles[0].Name,
+			cmd.CommandPath(),
+			profiles[0].Name,
+			profiles[0].Name,
+		)
+	}
+
+	return promptForProfileByHost(ctx, profiles, b.Config.Workspace.Host)
+}
+
 // configureBundle loads the bundle configuration and configures flag values, if any.
 func configureBundle(cmd *cobra.Command, b *bundle.Bundle) {
 	// Load bundle and select target.
@@ -96,9 +156,27 @@ func configureBundle(cmd *cobra.Command, b *bundle.Bundle) {
 	// is a fast operation. It does not perform network I/O or invoke processes (for example the Azure CLI).
 	client, err := b.WorkspaceClientE()
 	if err != nil {
-		logdiag.LogError(ctx, err)
-		return
+		names, isMulti := databrickscfg.AsMultipleProfiles(err)
+		if !isMulti {
+			logdiag.LogError(ctx, err)
+			return
+		}
+
+		selected, resolveErr := resolveProfileAmbiguity(cmd, b, err, names)
+		if resolveErr != nil {
+			logdiag.LogError(ctx, resolveErr)
+			return
+		}
+
+		b.Config.Workspace.Profile = selected
+		b.ClearWorkspaceClient()
+		client, err = b.WorkspaceClientE()
+		if err != nil {
+			logdiag.LogError(ctx, err)
+			return
+		}
 	}
+
 	ctx = cmdctx.SetConfigUsed(ctx, client.Config)
 	cmd.SetContext(ctx)
 }
diff --git a/cmd/root/bundle_test.go b/cmd/root/bundle_test.go
index 12fb667d8d..684117cbe3 100644
--- a/cmd/root/bundle_test.go
+++ b/cmd/root/bundle_test.go
@@ -7,9 +7,11 @@ import (
 	"path/filepath"
 	"runtime"
 	"testing"
+	"time"
 
 	"github.com/databricks/cli/internal/testutil"
 	"github.com/databricks/cli/libs/cmdctx"
+	"github.com/databricks/cli/libs/cmdio"
 	"github.com/databricks/cli/libs/diag"
 	"github.com/databricks/cli/libs/logdiag"
 	"github.com/spf13/cobra"
@@ -34,6 +36,7 @@ func setupDatabricksCfg(t *testing.T) {
 
 func emptyCommand(t *testing.T) *cobra.Command {
 	ctx := context.Background()
+	ctx = cmdio.MockDiscard(ctx)
 	cmd := &cobra.Command{}
 	cmd.SetContext(ctx)
 	initProfileFlag(cmd)
@@ -97,6 +100,8 @@ func TestBundleConfigureWithMultipleMatches(t *testing.T) {
 	diags := setupWithHost(t, cmd, "https://a.com")
 	require.Len(t, diags, 1)
 	assert.Contains(t, diags[0].Summary, "multiple profiles matched: PROFILE-1, PROFILE-2")
+	assert.Contains(t, diags[0].Summary, "Matching workspace profiles: PROFILE-1, PROFILE-2")
+	assert.Contains(t, diags[0].Summary, "DATABRICKS_CONFIG_PROFILE=PROFILE-1")
 }
 
 func TestBundleConfigureWithNonExistentProfileFlag(t *testing.T) {
@@ -217,6 +222,52 @@ func TestBundleConfigureProfileFlagAndEnvVariable(t *testing.T) {
 	assert.Equal(t, "PROFILE-2", cmdctx.ConfigUsed(cmd.Context()).Profile)
 }
 
+func TestBundleConfigureMultiMatchInteractivePromptFires(t *testing.T) {
+	testutil.CleanupEnvironment(t)
+
+	setupDatabricksCfg(t)
+
+	rootPath := t.TempDir()
+	testutil.Chdir(t, rootPath)
+
+	contents := `
+workspace:
+  host: "https://a.com"
+`
+	err := os.WriteFile(filepath.Join(rootPath, "databricks.yml"), []byte(contents), 0o644)
+	require.NoError(t, err)
+
+	ctx, cancel := context.WithTimeout(context.Background(), 3*time.Second)
+	defer cancel()
+
+	ctx, io := cmdio.SetupTest(ctx, cmdio.TestOptions{PromptSupported: true})
+	defer io.Done()
+
+	cmd := &cobra.Command{}
+	cmd.SetContext(ctx)
+	initProfileFlag(cmd)
+
+	done := make(chan struct{})
+	go func() {
+		defer close(done)
+		ctx := logdiag.InitContext(cmd.Context())
+		logdiag.SetCollect(ctx, true)
+		cmd.SetContext(ctx)
+		_ = MustConfigureBundle(cmd)
+	}()
+
+	// Verify the prompt fires by reading output from stderr.
+	// promptui with StartInSearchMode writes a search cursor first.
+	line, _, readErr := io.Stderr.ReadLine()
+	if assert.NoError(t, readErr, "expected prompt output on stderr") {
+		assert.Contains(t, string(line), "Search:")
+	}
+
+	// Cancel to unblock the prompt.
+	cancel()
+	<-done
+}
+
 func TestTargetFlagFull(t *testing.T) {
 	cmd := emptyCommand(t)
 	initTargetFlag(cmd)
diff --git a/libs/databrickscfg/loader.go b/libs/databrickscfg/loader.go
index 84c8398bfb..7566d19a4a 100644
--- a/libs/databrickscfg/loader.go
+++ b/libs/databrickscfg/loader.go
@@ -22,6 +22,16 @@ func (e errMultipleProfiles) Error() string {
 	return "multiple profiles matched: " + strings.Join(e, ", ")
 }
 
+// AsMultipleProfiles checks if the error is caused by multiple profiles
+// matching the same host. If so, it returns the matching profile names.
+func AsMultipleProfiles(err error) ([]string, bool) {
+	var e errMultipleProfiles
+	if errors.As(err, &e) {
+		return []string(e), true
+	}
+	return nil, false
+}
+
 func findMatchingProfile(configFile *config.File, matcher func(*ini.Section) bool) (*ini.Section, error) {
 	// Look for sections in the configuration file that match the configured host.
 	var matching []*ini.Section
diff --git a/libs/databrickscfg/loader_test.go b/libs/databrickscfg/loader_test.go
index c42fcdbdd1..425620abb5 100644
--- a/libs/databrickscfg/loader_test.go
+++ b/libs/databrickscfg/loader_test.go
@@ -1,10 +1,12 @@
 package databrickscfg
 
 import (
+	"errors"
 	"testing"
 
 	"github.com/databricks/databricks-sdk-go/config"
 	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
 )
 
 func TestLoaderSkipsEmptyHost(t *testing.T) {
@@ -133,3 +135,32 @@ func TestLoaderErrorsOnMultipleMatches(t *testing.T) {
 	assert.Error(t, err)
 	assert.ErrorContains(t, err, "https://foo: multiple profiles matched: foo1, foo2")
 }
+
+func TestAsMultipleProfilesExtractsNames(t *testing.T) {
+	cfg := config.Config{
+		Loaders: []config.Loader{
+			ResolveProfileFromHost,
+		},
+		ConfigFile: "profile/testdata/databrickscfg",
+		Host:       "https://foo/bar",
+	}
+
+	err := cfg.EnsureResolved()
+	require.Error(t, err)
+
+	names, ok := AsMultipleProfiles(err)
+	assert.True(t, ok)
+	assert.Equal(t, []string{"foo1", "foo2"}, names)
+}
+
+func TestAsMultipleProfilesReturnsFalseForUnrelatedError(t *testing.T) {
+	names, ok := AsMultipleProfiles(errors.New("some other error"))
+	assert.False(t, ok)
+	assert.Nil(t, names)
+}
+
+func TestAsMultipleProfilesReturnsFalseForNil(t *testing.T) {
+	names, ok := AsMultipleProfiles(nil)
+	assert.False(t, ok)
+	assert.Nil(t, names)
+}
diff --git a/libs/databrickscfg/profile/profiler.go b/libs/databrickscfg/profile/profiler.go
index 53ff7b305d..8eff2675b9 100644
--- a/libs/databrickscfg/profile/profiler.go
+++ b/libs/databrickscfg/profile/profiler.go
@@ -26,6 +26,18 @@ func MatchAllProfiles(p Profile) bool {
 	return true
 }
 
+// MatchProfileNames returns a match function that matches profiles by name.
+func MatchProfileNames(names ...string) ProfileMatchFunction {
+	nameSet := make(map[string]struct{}, len(names))
+	for _, n := range names {
+		nameSet[n] = struct{}{}
+	}
+	return func(p Profile) bool {
+		_, ok := nameSet[p.Name]
+		return ok
+	}
+}
+
 func WithName(name string) ProfileMatchFunction {
 	return func(p Profile) bool {
 		return p.Name == name
diff --git a/libs/databrickscfg/profile/profiler_test.go b/libs/databrickscfg/profile/profiler_test.go
index 75f4fa57d5..aa13e76a46 100644
--- a/libs/databrickscfg/profile/profiler_test.go
+++ b/libs/databrickscfg/profile/profiler_test.go
@@ -59,6 +59,20 @@ func TestWithHost(t *testing.T) {
 	}
 }
 
+func TestMatchProfileNames(t *testing.T) {
+	fn := MatchProfileNames("dev", "staging")
+
+	assert.True(t, fn(Profile{Name: "dev"}))
+	assert.True(t, fn(Profile{Name: "staging"}))
+	assert.False(t, fn(Profile{Name: "production"}))
+	assert.False(t, fn(Profile{Name: ""}))
+}
+
+func TestMatchProfileNamesEmpty(t *testing.T) {
+	fn := MatchProfileNames()
+	assert.False(t, fn(Profile{Name: "anything"}))
+}
+
 func TestWithHostAndAccountID(t *testing.T) {
 	cases := []struct {
 		name             string