diff --git a/contabo/lib/common.sh b/contabo/lib/common.sh
index 0f2fcc7ad..7072c6631 100644
--- a/contabo/lib/common.sh
+++ b/contabo/lib/common.sh
@@ -35,12 +35,22 @@ get_contabo_access_token() {
         -d "grant_type=password" \
         "${CONTABO_AUTH_URL}" 2>&1) || {
         log_error "Failed to obtain Contabo OAuth token"
-        log_error "Response: $response"
+        log_error ""
+        log_error "How to fix:"
+        log_error "  1. Verify your credentials at: https://my.contabo.com/api/details"
+        log_error "  2. Check that CONTABO_CLIENT_ID, CONTABO_CLIENT_SECRET, CONTABO_API_USER,"
+        log_error "     and CONTABO_API_PASSWORD are all set correctly"
+        log_error "  3. The API password is separate from your Contabo login password"
         return 1
     }
 
     if echo "$response" | grep -q '"error"'; then
-        log_error "OAuth authentication failed: $response"
+        log_error "Contabo OAuth authentication failed"
+        log_error ""
+        log_error "How to fix:"
+        log_error "  1. Verify credentials at: https://my.contabo.com/api/details"
+        log_error "  2. Ensure your API user has not been deactivated"
+        log_error "  3. Re-run to enter new credentials"
         return 1
     fi
 
@@ -48,7 +58,9 @@ get_contabo_access_token() {
     token=$(echo "$response" | python3 -c "import json,sys; print(json.loads(sys.stdin.read()).get('access_token',''))" 2>/dev/null)
 
     if [[ -z "$token" ]]; then
-        log_error "Failed to extract access token from response"
+        log_error "Failed to extract access token from Contabo OAuth response"
+        log_error "The API returned an unexpected response format."
+        log_error "Try again, or check Contabo's API status page."
         return 1
     fi
 
diff --git a/exoscale/lib/common.sh b/exoscale/lib/common.sh
index 73e68c25d..25e84b3a9 100644
--- a/exoscale/lib/common.sh
+++ b/exoscale/lib/common.sh
@@ -60,7 +60,9 @@ ensure_exo_cli() {
     local temp_dir
     temp_dir=$(mktemp -d)
     if ! curl -fsSL "$exo_url" -o "${temp_dir}/exo.tar.gz"; then
-        log_error "Failed to download exo CLI"
+        log_error "Failed to download exo CLI from: $exo_url"
+        log_error "Check your internet connection and try again."
+        log_error "You can also install manually: https://community.exoscale.com/documentation/tools/exoscale-command-line-interface/"
         rm -rf "$temp_dir"
         return 1
     fi
@@ -77,6 +79,7 @@ ensure_exo_cli() {
 test_exoscale_creds() {
     if ! exo config list &>/dev/null; then
         log_error "Exoscale credentials not configured or invalid"
+        log_error "Get your API credentials at: https://portal.exoscale.com/iam/api-keys"
         return 1
     fi
 
@@ -128,6 +131,11 @@ ensure_exoscale_creds() {
         return 0
     else
         log_error "Failed to configure Exoscale credentials"
+        log_error ""
+        log_error "How to fix:"
+        log_error "  1. Verify your API Key and Secret at: https://portal.exoscale.com/iam/api-keys"
+        log_error "  2. Ensure the API key has the required permissions (compute, SSH keys)"
+        log_error "  3. Re-run the command to enter new credentials"
         return 1
     fi
 }
diff --git a/netcup/lib/common.sh b/netcup/lib/common.sh
index fbe377cf3..5bfa63767 100644
--- a/netcup/lib/common.sh
+++ b/netcup/lib/common.sh
@@ -72,6 +72,7 @@ netcup_get_session() {
         -H "Content-Type: application/json" \
         -d "$body" 2>&1) || {
         log_error "Failed to connect to Netcup API"
+        log_error "Check your internet connection and try again."
         return 1
     }
 
diff --git a/scaleway/lib/common.sh b/scaleway/lib/common.sh
index 6282cce0c..3741ced4a 100644
--- a/scaleway/lib/common.sh
+++ b/scaleway/lib/common.sh
@@ -88,7 +88,11 @@ get_scaleway_project_id() {
 
     if [[ -z "$project_id" ]]; then
         log_error "Failed to get Scaleway project ID"
-        log_warn "Set SCW_DEFAULT_PROJECT_ID environment variable or check API permissions"
+        log_error ""
+        log_error "How to fix:"
+        log_error "  1. Set SCW_DEFAULT_PROJECT_ID in your environment"
+        log_error "  2. Find your Project ID at: https://console.scaleway.com/project/settings"
+        log_error "  3. Ensure your API key has permission to list projects"
         return 1
     fi
 
diff --git a/shared/common.sh b/shared/common.sh
index 26cccfeba..69f38be97 100644
--- a/shared/common.sh
+++ b/shared/common.sh
@@ -122,24 +122,33 @@ ensure_jq() {
 
     if [[ "$OSTYPE" == "darwin"* ]]; then
         if command -v brew &>/dev/null; then
-            brew install jq || { log_error "Failed to install jq via Homebrew"; return 1; }
+            brew install jq || { log_error "Failed to install jq via Homebrew. Run 'brew install jq' manually."; return 1; }
         else
-            log_error "Install jq: brew install jq (or https://jqlang.github.io/jq/download/)"
+            log_error "jq is required but not installed"
+            log_error "Install it with: brew install jq"
+            log_error "If Homebrew is not available: https://jqlang.github.io/jq/download/"
             return 1
         fi
     elif command -v apt-get &>/dev/null; then
-        sudo apt-get update -qq && sudo apt-get install -y jq || { log_error "Failed to install jq via apt"; return 1; }
+        sudo apt-get update -qq && sudo apt-get install -y jq || { log_error "Failed to install jq via apt. Run 'sudo apt-get install -y jq' manually."; return 1; }
     elif command -v dnf &>/dev/null; then
-        sudo dnf install -y jq || { log_error "Failed to install jq via dnf"; return 1; }
+        sudo dnf install -y jq || { log_error "Failed to install jq via dnf. Run 'sudo dnf install -y jq' manually."; return 1; }
     elif command -v apk &>/dev/null; then
-        sudo apk add jq || { log_error "Failed to install jq via apk"; return 1; }
+        sudo apk add jq || { log_error "Failed to install jq via apk. Run 'sudo apk add jq' manually."; return 1; }
     else
-        log_error "jq is required but not installed. Install from https://jqlang.github.io/jq/download/"
+        log_error "jq is required but not installed"
+        log_error ""
+        log_error "Install jq for your system:"
+        log_error "  Ubuntu/Debian:  sudo apt-get install -y jq"
+        log_error "  Fedora/RHEL:    sudo dnf install -y jq"
+        log_error "  macOS:          brew install jq"
+        log_error "  Other:          https://jqlang.github.io/jq/download/"
         return 1
     fi
 
     if ! command -v jq &>/dev/null; then
-        log_error "jq not found in PATH after installation"
+        log_error "jq was installed but is not found in PATH"
+        log_error "Try opening a new terminal or run: hash -r"
         return 1
     fi
 
@@ -444,7 +453,12 @@ get_openrouter_api_key_manual() {
     while [[ -z "${api_key}" ]]; do
         attempts=$((attempts + 1))
         if [[ ${attempts} -gt ${max_attempts} ]]; then
-            log_error "Too many failed attempts. Set OPENROUTER_API_KEY environment variable and try again."
+            log_error "Too many failed attempts."
+            log_error ""
+            log_error "How to fix:"
+            log_error "  1. Get your key from: https://openrouter.ai/settings/keys"
+            log_error "  2. Set it before running spawn: export OPENROUTER_API_KEY=sk-or-v1-..."
+            log_error "  3. Then re-run: spawn <agent> <cloud>"
             return 1
         fi
         api_key=$(safe_read "Enter your OpenRouter API key: ") || return 1
@@ -1033,9 +1047,21 @@ generate_ssh_key_if_missing() {
     if [[ -f "${key_path}" ]]; then
         return 0
     fi
-    log_step "Generating SSH key..."
-    mkdir -p "$(dirname "${key_path}")"
-    ssh-keygen -t ed25519 -f "${key_path}" -N "" -q
+    log_step "Generating SSH key at ${key_path}..."
+    mkdir -p "$(dirname "${key_path}")" || {
+        log_error "Failed to create SSH key directory: $(dirname "${key_path}")"
+        log_error "Check that you have write permissions to this directory."
+        return 1
+    }
+    ssh-keygen -t ed25519 -f "${key_path}" -N "" -q || {
+        log_error "Failed to generate SSH key at ${key_path}"
+        log_error ""
+        log_error "How to fix:"
+        log_error "  1. Check disk space: df -h $(dirname "${key_path}")"
+        log_error "  2. Check permissions: ls -la $(dirname "${key_path}")"
+        log_error "  3. Generate manually: ssh-keygen -t ed25519 -f ${key_path}"
+        return 1
+    }
     log_info "SSH key generated at ${key_path}"
 }
 
@@ -1043,7 +1069,21 @@ generate_ssh_key_if_missing() {
 # Usage: get_ssh_fingerprint PUB_KEY_PATH
 get_ssh_fingerprint() {
     local pub_path="${1}"
-    ssh-keygen -lf "${pub_path}" -E md5 2>/dev/null | awk '{print $2}' | sed 's/MD5://'
+    if [[ ! -f "${pub_path}" ]]; then
+        log_error "SSH public key not found: ${pub_path}"
+        log_error "Expected a public key file alongside your private key."
+        log_error "Regenerate with: ssh-keygen -t ed25519 -f ${pub_path%.pub}"
+        return 1
+    fi
+    local fingerprint
+    fingerprint=$(ssh-keygen -lf "${pub_path}" -E md5 2>/dev/null | awk '{print $2}' | sed 's/MD5://')
+    if [[ -z "${fingerprint}" ]]; then
+        log_error "Failed to read SSH public key fingerprint from ${pub_path}"
+        log_error "The key file may be corrupted or in an unsupported format."
+        log_error "Regenerate with: ssh-keygen -t ed25519 -f ${pub_path%.pub}"
+        return 1
+    fi
+    echo "${fingerprint}"
 }
 
 # JSON-escape a string (for embedding in JSON bodies)
@@ -1255,7 +1295,13 @@ _report_api_failure() {
     local max_retries="${2}"
     log_error "${retry_reason} after ${max_retries} attempts"
     if [[ "${retry_reason}" == "Cloud API network error" ]]; then
-        log_warn "Check your internet connection and verify the provider's API is reachable."
+        log_warn "Could not reach the cloud provider's API."
+        log_warn ""
+        log_warn "How to fix:"
+        log_warn "  1. Check your internet connection: curl -s https://httpbin.org/ip"
+        log_warn "  2. Check DNS resolution: nslookup the provider's API hostname"
+        log_warn "  3. If behind a proxy or firewall, ensure HTTPS traffic is allowed"
+        log_warn "  4. Try again in a few moments (the API may be temporarily down)"
     else
         log_warn "This is usually caused by rate limiting or temporary provider issues."
         log_warn "Wait a minute and try again, or check the provider's status page."
@@ -1468,8 +1514,15 @@ generic_ssh_wait() {
         attempt=$((attempt + 1))
     done
 
-    log_error "${description} timed out after ${elapsed_time}s"
-    log_warn "The server at ${ip} may still be booting. You can try again or check its status in your cloud provider dashboard."
+    log_error "${description} timed out after ${elapsed_time}s (server: ${ip})"
+    log_warn ""
+    log_warn "The server may still be booting or the connection may be blocked."
+    log_warn ""
+    log_warn "How to fix:"
+    log_warn "  1. Re-run the command to try again (the server may need more time)"
+    log_warn "  2. Check your cloud provider dashboard to verify the server is running"
+    log_warn "  3. Test SSH manually: ssh ${username}@${ip}"
+    log_warn "  4. Check that port 22 is open in the server's firewall/security group"
     return 1
 }