diff --git a/.github/workflows/coder.yaml b/.github/workflows/coder.yaml
index 39a20bba18348..bd6d6f5753939 100644
--- a/.github/workflows/coder.yaml
+++ b/.github/workflows/coder.yaml
@@ -209,7 +209,7 @@ jobs:
         run: gotestsum --junitfile="gotests.xml" --packages="./..." --
           -covermode=atomic -coverprofile="gotests.coverage"
           -coverpkg=./...,github.com/coder/coder/codersdk
-          -timeout=3m -count=$GOCOUNT -short -failfast
+          -timeout=5m -count=$GOCOUNT -short -failfast
 
       - name: Upload DataDog Trace
         if: always() && github.actor != 'dependabot[bot]' && !github.event.pull_request.head.repo.fork
@@ -316,7 +316,7 @@ jobs:
   deploy:
     name: "deploy"
     runs-on: ubuntu-latest
-    timeout-minutes: 20
+    timeout-minutes: 30
     if: github.ref == 'refs/heads/main' && !github.event.pull_request.head.repo.fork
     permissions:
       contents: read
diff --git a/Makefile b/Makefile
index a75a9cb2884c9..ed8584bad7eb9 100644
--- a/Makefile
+++ b/Makefile
@@ -115,7 +115,7 @@ test: test-clean
 .PHONY: test-postgres
 test-postgres: test-clean
 	DB=ci gotestsum --junitfile="gotests.xml" --packages="./..." -- \
-          -covermode=atomic -coverprofile="gotests.coverage" -timeout=5m \
+          -covermode=atomic -coverprofile="gotests.coverage" -timeout=10m \
           -coverpkg=./...,github.com/coder/coder/codersdk \
           -count=1 -parallel=1 -race -failfast
 
diff --git a/cli/server_test.go b/cli/server_test.go
index 1a3ff7ee3bdf6..cb343547f93c1 100644
--- a/cli/server_test.go
+++ b/cli/server_test.go
@@ -56,7 +56,7 @@ func TestServer(t *testing.T) {
 			assert.NoError(t, err)
 			client = codersdk.New(accessURL)
 			return true
-		}, 15*time.Second, 25*time.Millisecond)
+		}, time.Minute, 50*time.Millisecond)
 		_, err = client.CreateFirstUser(ctx, codersdk.CreateFirstUserRequest{
 			Email:            "some@one.com",
 			Username:         "example",