diff --git a/OmniBLE/PumpManager/OmniBLEPumpManager.swift b/OmniBLE/PumpManager/OmniBLEPumpManager.swift
index 35b400ca..ada8e522 100644
--- a/OmniBLE/PumpManager/OmniBLEPumpManager.swift
+++ b/OmniBLE/PumpManager/OmniBLEPumpManager.swift
@@ -888,6 +888,7 @@ extension OmniBLEPumpManager {
                     self.podComms.pairAndSetupPod(timeZone: .currentFixed, insulinType: insulinType, messageLogger: self)
                     { (result) in
 
+                        // Have new podState, reset all the per pod pump manager state
                         self.resetPerPodPumpManagerState()
 
                         // Calls completion
@@ -900,6 +901,9 @@ extension OmniBLEPumpManager {
         } else {
             self.log.default("Pod already paired. Continuing.")
 
+            // Resuming the pod setup, try to ensure pod comms will work right away
+            self.resumingPodSetup()
+
             self.podComms.runSession(withName: "Prime pod") { (result) in
                 // Calls completion
                 primeSession(result)
@@ -959,6 +963,10 @@ extension OmniBLEPumpManager {
         self.podComms.runSession(withName: "Insert cannula") { (result) in
             switch result {
             case .success(let session):
+                if self.state.podState?.setupProgress.cannulaInsertionSuccessfullyStarted == true {
+                    // Resuming the pod setup, try to ensure pod comms will work right away
+                    self.resumingPodSetup()
+                }
                 do {
                     if self.state.podState?.setupProgress.needsInitialBasalSchedule == true {
                         let scheduleOffset = timeZone.scheduleOffset(forDate: Date())
@@ -1011,6 +1019,33 @@ extension OmniBLEPumpManager {
         #endif
     }
 
+    // Called when resuming a pod setup operation which sometimes can fail on the first pod command in various situations.
+    // Attempting a getStatus and sleeping a couple of seconds on errors greatly improves the odds for first pod command success.
+    public func resumingPodSetup() {
+        let sleepTime:UInt32 = 2
+
+        if !isConnected {
+            self.log.debug("### Pod setup resume pod not connected, sleeping %d seconds", sleepTime)
+            sleep(sleepTime)
+        }
+
+        podComms.runSession(withName: "Resuming pod setup") { (result) in
+            switch result {
+            case .success(let session):
+                let status = try? session.getStatus()
+                if status == nil {
+                    self.log.debug("### Pod setup resume getStatus failed, sleeping %d seconds", sleepTime)
+                    sleep(sleepTime)
+                }
+            case .failure(let error):
+                self.log.debug("### Pod setup resume session failure, sleeping %d seconds: %@", sleepTime, error.localizedDescription)
+                sleep(sleepTime)
+            }
+        }
+    }
+
+    // MARK: - Pump Commands
+
     public func getPodStatus(completion: ((_ result: PumpManagerResult<StatusResponse>) -> Void)? = nil) {
         guard state.hasActivePod else {
             completion?(.failure(PumpManagerError.configuration(OmniBLEPumpManagerError.noPodPaired)))
@@ -1038,8 +1073,6 @@ extension OmniBLEPumpManager {
         }
     }
 
-    // MARK: - Pump Commands
-
     public func acknowledgePodAlerts(_ alertsToAcknowledge: AlertSet, completion: @escaping (_ alerts: [AlertSlot: PodAlert]?) -> Void) {
         guard self.hasActivePod else {
             completion(nil)
diff --git a/OmniBLE/PumpManagerUI/ViewModels/InsertCannulaViewModel.swift b/OmniBLE/PumpManagerUI/ViewModels/InsertCannulaViewModel.swift
index 984a507b..733fc36b 100644
--- a/OmniBLE/PumpManagerUI/ViewModels/InsertCannulaViewModel.swift
+++ b/OmniBLE/PumpManagerUI/ViewModels/InsertCannulaViewModel.swift
@@ -129,6 +129,7 @@ class InsertCannulaViewModel: ObservableObject, Identifiable {
     }
 
     @Published var state: InsertCannulaViewModelState = .ready
+
     public var stateNeedsDeliberateUserAcceptance : Bool {
         switch state {
         case .ready:
@@ -143,16 +144,19 @@ class InsertCannulaViewModel: ObservableObject, Identifiable {
     var didRequestDeactivation: (() -> Void)?
     
     var cannulaInserter: CannulaInserter
-    
+
+    var autoRetryAttempted: Bool
+
     init(cannulaInserter: CannulaInserter) {
         self.cannulaInserter = cannulaInserter
+        self.autoRetryAttempted = false
 
         // If resuming, don't wait for the button action
         if cannulaInserter.cannulaInsertionSuccessfullyStarted {
             insertCannula()
         }
     }
-    
+
     private func checkCannulaInsertionFinished() {
         state = .checkingInsertion
         cannulaInserter.checkCannulaInsertionFinished() { (error) in
@@ -168,6 +172,7 @@ class InsertCannulaViewModel: ObservableObject, Identifiable {
     
     private func insertCannula() {
         state = .startingInsertion
+
         cannulaInserter.insertCannula { (result) in
             DispatchQueue.main.async {
                 switch(result) {
@@ -182,7 +187,19 @@ class InsertCannulaViewModel: ObservableObject, Identifiable {
                         self.state = .finished
                     }
                 case .failure(let error):
-                    self.state = .error(error)
+                    if self.autoRetryAttempted {
+                        self.autoRetryAttempted = false // allow for an auto retry on the next user attempt
+                        self.state = .error(error)
+                    } else {
+                        self.autoRetryAttempted = true
+                        let autoRetryPauseTime = TimeInterval(seconds: 3)
+                        print("### insertCannula encountered error \(error.localizedDescription), retrying after \(autoRetryPauseTime) seconds")
+                        DispatchQueue.global(qos: .utility).async {
+                            Thread.sleep(forTimeInterval: autoRetryPauseTime)
+
+                            self.insertCannula()
+                        }
+                    }
                 }
             }
         }
diff --git a/OmniBLE/PumpManagerUI/ViewModels/PairPodViewModel.swift b/OmniBLE/PumpManagerUI/ViewModels/PairPodViewModel.swift
index 5e1ce70b..4e3ec324 100644
--- a/OmniBLE/PumpManagerUI/ViewModels/PairPodViewModel.swift
+++ b/OmniBLE/PumpManagerUI/ViewModels/PairPodViewModel.swift
@@ -168,8 +168,11 @@ class PairPodViewModel: ObservableObject, Identifiable {
 
     var podPairer: PodPairer
 
+    var autoRetryAttempted: Bool
+
     init(podPairer: PodPairer) {
         self.podPairer = podPairer
+        self.autoRetryAttempted = false
 
         // If resuming, don't wait for the button action
         if podPairer.podCommState == .activating {
@@ -189,8 +192,20 @@ class PairPodViewModel: ObservableObject, Identifiable {
             DispatchQueue.main.async {
                 switch status {
                 case .failure(let error):
-                    let pairingError = DashPairingError.pumpManagerError(error)
-                    self.state = .error(pairingError)
+                    if self.autoRetryAttempted {
+                        self.autoRetryAttempted = false // allow for an auto retry on the next user attempt
+                        let pairAndPrimeError = DashPairingError.pumpManagerError(error)
+                        self.state = .error(pairAndPrimeError)
+                    } else {
+                        self.autoRetryAttempted = true
+                        let autoRetryPauseTime = TimeInterval(seconds: 3)
+                        print("### pairAndPrimePod encountered error \(error.localizedDescription), retrying after \(autoRetryPauseTime) seconds")
+                        DispatchQueue.global(qos: .utility).async {
+                            Thread.sleep(forTimeInterval: autoRetryPauseTime)
+
+                            self.pairAndPrime() // handles both pairing or priming failures
+                        }
+                    }
                 case .success(let duration):
                     
                     if duration > 0 {