diff --git a/internal/command/meta_backend.go b/internal/command/meta_backend.go
index 4e0b09555..825de47e6 100644
--- a/internal/command/meta_backend.go
+++ b/internal/command/meta_backend.go
@@ -97,14 +97,6 @@ func (m *Meta) Backend(opts *BackendOpts) (backend.Enhanced, tfdiags.Diagnostics
 		b, backendDiags = m.backendFromConfig(opts)
 		diags = diags.Append(backendDiags)
 
-		if opts.Init && b != nil && !diags.HasErrors() {
-			// Its possible that the currently selected workspace doesn't exist, so
-			// we call selectWorkspace to ensure an existing workspace is selected.
-			if err := m.selectWorkspace(b); err != nil {
-				diags = diags.Append(err)
-			}
-		}
-
 		if diags.HasErrors() {
 			return nil, diags
 		}
@@ -232,8 +224,11 @@ func (m *Meta) selectWorkspace(b backend.Backend) error {
 				Query:       "\n[reset][bold][yellow]No workspaces found.[reset]",
 				Description: fmt.Sprintf(inputCloudInitCreateWorkspace, strings.Join(c.WorkspaceMapping.Tags, ", ")),
 			})
+			if err != nil {
+				return fmt.Errorf("Couldn't create initial workspace: %w", err)
+			}
 			name = strings.TrimSpace(name)
-			if err != nil || name == "" {
+			if name == "" {
 				return fmt.Errorf("Couldn't create initial workspace: no name provided")
 			}
 			log.Printf("[TRACE] Meta.selectWorkspace: selecting the new TFC workspace requested by the user (%s)", name)
@@ -610,7 +605,7 @@ func (m *Meta) backendFromConfig(opts *BackendOpts) (backend.Backend, tfdiags.Di
 
 		return m.backend_c_r_S(c, cHash, sMgr, true)
 
-	// Configuring a backend for the first time.
+	// Configuring a backend for the first time or -reconfigure flag was used
 	case c != nil && s.Backend.Empty():
 		log.Printf("[TRACE] Meta.Backend: moving from default local state only to %q backend", c.Type)
 		if !opts.Init {
@@ -631,9 +626,7 @@ func (m *Meta) backendFromConfig(opts *BackendOpts) (backend.Backend, tfdiags.Di
 			}
 			return nil, diags
 		}
-
-		return m.backend_C_r_s(c, cHash, sMgr)
-
+		return m.backend_C_r_s(c, cHash, sMgr, opts)
 	// Potentially changing a backend configuration
 	case c != nil && !s.Backend.Empty():
 		// We are not going to migrate if...
@@ -643,7 +636,15 @@ func (m *Meta) backendFromConfig(opts *BackendOpts) (backend.Backend, tfdiags.Di
 		// AND we're not providing any overrides. An override can mean a change overriding an unchanged backend block (indicated by the hash value).
 		if (uint64(cHash) == s.Backend.Hash) && (!opts.Init || opts.ConfigOverride == nil) {
 			log.Printf("[TRACE] Meta.Backend: using already-initialized, unchanged %q backend configuration", c.Type)
-			return m.savedBackend(sMgr)
+			savedBackend, diags := m.savedBackend(sMgr)
+			// Verify that selected workspace exist. Otherwise prompt user to create one
+			if opts.Init && savedBackend != nil {
+				if err := m.selectWorkspace(savedBackend); err != nil {
+					diags = diags.Append(err)
+					return nil, diags
+				}
+			}
+			return savedBackend, diags
 		}
 
 		// If our configuration (the result of both the literal configuration and given
@@ -665,6 +666,13 @@ func (m *Meta) backendFromConfig(opts *BackendOpts) (backend.Backend, tfdiags.Di
 			if moreDiags.HasErrors() {
 				return nil, diags
 			}
+			// Verify that selected workspace exist. Otherwise prompt user to create one
+			if opts.Init && savedBackend != nil {
+				if err := m.selectWorkspace(savedBackend); err != nil {
+					diags = diags.Append(err)
+					return nil, diags
+				}
+			}
 
 			return savedBackend, diags
 		}
@@ -685,7 +693,7 @@ func (m *Meta) backendFromConfig(opts *BackendOpts) (backend.Backend, tfdiags.Di
 		}
 
 		log.Printf("[WARN] backend config has changed since last init")
-		return m.backend_C_r_S_changed(c, cHash, sMgr, true)
+		return m.backend_C_r_S_changed(c, cHash, sMgr, true, opts)
 
 	default:
 		diags = diags.Append(fmt.Errorf(
@@ -897,7 +905,7 @@ func (m *Meta) backend_c_r_S(c *configs.Backend, cHash int, sMgr *clistate.Local
 }
 
 // Configuring a backend for the first time.
-func (m *Meta) backend_C_r_s(c *configs.Backend, cHash int, sMgr *clistate.LocalState) (backend.Backend, tfdiags.Diagnostics) {
+func (m *Meta) backend_C_r_s(c *configs.Backend, cHash int, sMgr *clistate.LocalState, opts *BackendOpts) (backend.Backend, tfdiags.Diagnostics) {
 	var diags tfdiags.Diagnostics
 
 	// Grab a purely local backend to get the local state if it exists
@@ -1017,6 +1025,14 @@ func (m *Meta) backend_C_r_s(c *configs.Backend, cHash int, sMgr *clistate.Local
 		Hash:      uint64(cHash),
 	}
 
+	// Verify that selected workspace exist. Otherwise prompt user to create one
+	if opts.Init && b != nil {
+		if err := m.selectWorkspace(b); err != nil {
+			diags = diags.Append(err)
+			return nil, diags
+		}
+	}
+
 	if err := sMgr.WriteState(s); err != nil {
 		diags = diags.Append(fmt.Errorf(errBackendWriteSaved, err))
 		return nil, diags
@@ -1037,7 +1053,7 @@ func (m *Meta) backend_C_r_s(c *configs.Backend, cHash int, sMgr *clistate.Local
 }
 
 // Changing a previously saved backend.
-func (m *Meta) backend_C_r_S_changed(c *configs.Backend, cHash int, sMgr *clistate.LocalState, output bool) (backend.Backend, tfdiags.Diagnostics) {
+func (m *Meta) backend_C_r_S_changed(c *configs.Backend, cHash int, sMgr *clistate.LocalState, output bool, opts *BackendOpts) (backend.Backend, tfdiags.Diagnostics) {
 	var diags tfdiags.Diagnostics
 
 	// Get the old state
@@ -1133,6 +1149,14 @@ func (m *Meta) backend_C_r_S_changed(c *configs.Backend, cHash int, sMgr *clista
 		Hash:      uint64(cHash),
 	}
 
+	// Verify that selected workspace exist. Otherwise prompt user to create one
+	if opts.Init && b != nil {
+		if err := m.selectWorkspace(b); err != nil {
+			diags = diags.Append(err)
+			return b, diags
+		}
+	}
+
 	if err := sMgr.WriteState(s); err != nil {
 		diags = diags.Append(fmt.Errorf(errBackendWriteSaved, err))
 		return nil, diags